Organic compounds

ABSTRACT

The invention relates to compounds of formula I  
                 
 
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 8′ , R 9 , W, X, A 1 , A 2 , a, b and c have the significances given in the specification, and optionally the enantiomers thereof. The active ingredients have advantageous pesticidal properties. They are especially suitable for controlling parasites on warm-blooded animals.

The present invention relates to new amidoacetonitrile compounds offormula

wherein

-   -   A₁ and A₂, independently of one another, signify unsubstituted        aryl or aryl which is substituted once or many times, whereby        the substituents of A₁ and A₂, independently of one another, are        selected from the group consisting of halogen, nitro, cyano,        C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,        C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl        C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy,        C₁-C₆-alkylthio, halo-C₁-C₈-alkylthio, C₁-C₆-alkylsulfonyloxy,        halo-C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylsulfinyl,        halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,        halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylthio,        halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl,        halo-C₂-C₆-alkenylsulfinyl, C₂-C₆-alkenylsulfonyl,        halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino,        di-C₁-C₆-alkylamino, C₁-C₆-alkylsulfonylamino,        halo-C₁-C₆-alkylsulfonylamino, C₁-C₆-alkylcarbonyl,        halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,        C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl,        unsubstituted phenylamino or phenylamino which is substituted        once or many times, unsubstituted phenylcarbonyl or        phenylcarbonyl which is substituted once or many times,        unsubstituted phenylmethoximino phenylhydroxymethyl or        phenylhydroxymethyl which is substituted once or many times,        unsubstituted 1-phenyl-1-hydroxyethyl or 1-phenyl-1-hydroxyethyl        which is substituted once or many times, unsubstituted        phenylchloromethyl or phenylchloromethyl which is substituted        once or many times, unsubstituted phenylcyanomethyl or        phenylcyanomethyl which is substituted once or many times,        unsubstituted phenyl or phenyl which is substituted once or many        times; unsubstituted phenoxy or phenoxy which is substituted        once or many times; unsubstituted phenyacetylenyl or        phenyacetylenyl which is substituted once or many times, and        unsubstituted pyridyloxy or pyddyloxy which is substituted once        or many times, whereby the substituents may each be independent        of one another and are selected from R₉; or unsubstituted        hetaryl or hetaryl which is substituted once or many times and        is bound by a ring carbon atom, whereby the substituents of A₁        and A₂ may be independent of one another and are selected from        R₉;    -   R₁ signifies hydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, allyl or        C₁-C₆-alkoxymethyl;    -   R₂, R₃, R₄, R₅ and R₆ are either, independently of one another,        hydrogen, halogen, unsubstituted C₁-C₆-alkyl or C₁-C₆-alkyl        which is substituted once or many times, unsubstituted        C₂-C₆-alkenyl or C₂-C₆-alkenyl which is substituted once or many        times, unsubstituted C₂-C₆-alkinyl or C₂-C₆-alkinyl which is        substituted once or many times, unsubstituted C₁-C₆-alkoxy or        C₁-C₆-alkoxy which is substituted once or many times, whereby        the substituents may each be independent of one another and are        selected from the group consisting of halogen, C₁-C₆-alkoxy und        halo-C₁-C₆₋alkoxy; unsubstituted C₃-C₆-cycloalkyl or        C₃-C₆-cycloalkyl which is substituted once or many times,        whereby the substituents may be independent of one another and        are selected from the group consisting of halogen and        C₁-C₆-alkyl; or unsubstituted phenyl or phenyl which is        substituted once or many times, whereby the substituents may be        independent of one another and are selected from the group        consisting of halogen, nitro, cyano, C₁-C₆-alkyl,        halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,        C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,        halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,        halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino or        di-C₁-C₆-alkylamino;    -   or R₂ and R₃ together signify C₂-C₆-alkylene;    -   R₇ signifies hydrogen or C₁-C₆-alkyl;    -   either R₈ signifies C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,        C₃-C₈-cycloalkyl, halo-C₃-C₈-cycloalkyl, C₃-C₈-cycloalkylamino,        halo-C₃-C₈-cycloalkylamino, C₃-C₈-cycloalkoxy,        halo-C₃-C₈-cycloalkoxy or C₃-C₈-cycloalkylthio; and R_(8′)        signifies hydrogen or R₉;    -   or R₈ and R_(8′) together signify unsubstituted or unsubstituted        C₃-C₅-alkylene, whereby one or two carbon atoms may be replaced        by O, N or S;    -   R₉ signifies halogen, nitro, cyano, C₁-C₆-alkyl,        halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,        C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cyloalkylamino,        C₃-C₆-cycloalkylthio, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy,        C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyloxy,        halo-C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylsulfinyl,        halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,        halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylthio,        halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl,        halo-C₂-C₆-alkenylsulfinyl, C₂-C₆-alkenylsulfonyl,        halo-C₂-C₆alkenylsulfonyl, C₁-C₆-alkylamino,        di-C₁-C₆-alkylamino, C₁-C₆-alkylsulfonylamino,        halo-C₁-C₆-alkylsulfonylamino, C₁-C₆-alkylcarbonyl,        halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,        C₁-C₆-alkylaminocarbonyl or di-C₁-C₆-alkylaminocarbonyl;    -   W signifies O, S, S(O₂) or N(R₇);    -   X signifies O or N(R₇);    -   a signifies 1, 2, 3 or 4;    -   b signifies 0, 1, 2, 3 or 4; and    -   c is 0 or 1;        optionally diastereoisomers, ErZ-isomers, E/Z-isomer mixtures        and/or tautomers, each respectively in free form or in salt        form, their preparation and usage in the control of endo- and        ectoparasites, especially helminths, in and on warm-blooded        animals, especially productive livestock and domestic animals,        as well as on plants, furthermore pesticides which contain at        least one of these compounds.

Substituted amidoacetonitrile compounds having pesticidal activity aredescribed for example in EP-0.953.565 A2. However, the activeingredients specifically disclosed therein cannot always fulfil therequirements regarding potency and activity spectrum. There is thereforea need for active ingredients with improved pesticidal properties. Ithas now been found that the amidoacetonitrile compounds of formula Ihave excellent pesticidal properties, especially against endo- andecto-parasites in and on warm-blooded animals and plants.

Alkyl—as a group per se and as structural element of other groups andcompounds, for example halogen-alkyl, alkoxy, alkylthio, alkylsulfinyland alkylsulfonyl,—is, in each case with due consideration of thespecific number of carbon atoms in the group or compound in question,either straight-chained, i.e. methyl, ethyl, propyl, butyl, pentyl orhexyl, or branched, e.g. isopropyl, isobutyl, sec.-butyl, tert.-butyl,isopentyl, neopentyl or isohexyl.

Alkenyl—as a group per se and as structural element of other groups andcompounds—is, in each case with due consideration of the specific numberof carbon atoms in the group or compound in question and of theconjugated or isolated double bonds—either straight-chained, e.g. allyl,2-butenyl, 3-pentenyl, 1-hexenyl or 1,3-hexadienyl, or branched, e.g.isopropenyl, isobutenyl, isoprenyl, tert.-pentenyl or isohexenyl.

Alkinyl—as a group per se and as structural element of other groups andcompounds—is, in each case with due consideration of the specific numberof carbon atoms in the group or compound in question and of theconjugated or isolated double bonds—either straight-chained, e.g.propargyl, 2-butinyl, 3pentinyl, 1-hexinyl, 1-heptinyl or 3hexen-1-inyl,or branched, e.g. 3methylbut-1-inyl, 4-ethylpent-1-inyl or4-methylhex-2-inyl.

Cycloalkyl—as a group per se and as structural element of other groupsand compounds such as halocycloalkyl, cycloalkoxy or cycloalkylthio,—is,in each case with due consideration of the specific number of carbonatoms in the group or compound in question, cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl.

Aryl is phenyl or naphthyl.

Hetaryl is pyridyl, pyrimidyl, s-triazinyl, 1,2,4-triazinyl, thienyl,furanyl, pyrryl, pyrazolyl, imidazoyl, thiazolyl, triazolyl, oxazolyl,thiadiazolyl, oxadiazolyl, benzothienyl, benzofuranyl, benzothiazolyl,indoly, indazolyl or quinolyl.

Halogen—as a group per se and as structural element of other groups andcompounds such as haloalkyl, haloalkoxy, haloalkylthio,haloalkylsulfinyl and haloalkylsulfonyl—is fluorine, chlorine, bromineor iodine, especially fluorine, chlorine or bromine, in particularfluorine or chlorine.

Halogen-substituted carbon-containing groups and compounds, such ashaloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl andhaloalkylsulfonyl, may be partially halogenated or perhalogenated,whereby in the case of multiple halogenation, the halogen substituentsmay be identical or different. Examples of halogen-alkyl—as a group perse and as structural element of other groups and compounds such ashaloalkoxy or haloalkylthio,—are methyl which is mono- to trisubstitutedby fluorine, chlorine and/or bromine, such as CHF₂ or CF₃; ethyl whichis mono- to pentasubstituted by fluorine, chlorine and/or bromine, suchas CH₂CF₃, CF₂CF₃, CF₂CCl₃, CF₂CHCl₂, CF₂CHF₂, CF₂CFCl₂, CF₂CHBr₂,CF₂CHClF, CF₂CHBrF or CClFCHClF; propyl or isopropyl, mono- toheptasubstituted by fluorine, chlorine and/or bromine, such asCH₂CHBrCH₂Br, CF₂CHFCF₃, CH₂CF₂CF₃ or CH(CF₃)₂; butyl or one of itsisomers, mono- to nonasubstituted by fluorine, chlorine and/or bromine,such as CF(CF₃)CHFCF₃ or CH₂(CF₂)₂CF₃; pentyl or one of its isomerssubstituted once to eleven times by fluorine, chlorine and/or bromine,such as CF(CF₃)(CHF)₂CF₃ or CH₂(CF₂)₃CF₃; and hexyl or one of itsisomers substituted once to thirteen times by fluorine, chlorine and/orbromine, such as (CH₂)₄CHBrCH₂Br, CF₂(CHF)₄CF₃, CH₂(CF₂)₄CF₃ orC(CF₃)₂(CHF)₂CF₃.

Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms.Alkoxy is for example methoxy, ethoxy, propoxy, isopropoxy, n-butoxy,isobutoxy, sec.-butoxy and tert.-butoxy, as well as the isomerspentyloxy and hexyloxy; preferably methoxy and ethoxy. Haloalkoxy groupspreferably have a chain length of 1 to 6 carbon atoms. Haloalkoxy ise.g. fluoromethoxy, difluoromethoxy, trifluoromethoxy,2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy,2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferablydifluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Preferredembodiments within the scope of the invention are:

-   -   (1) A compound of formula I, wherein A₁ and A₂, independently of        one another, signify aryl which is unsubstituted or substituted        once or many times, whereby the substituents of A₁ and A₂,        independently of one another, are selected from the group        consisting of halogen, nitro, cyano, C₁-C₆-alkyl,        halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,        C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy,        C₁-C₆alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl,        halo-C₁-C₆-aralkylsulfonyl, C₁-C₆-alkylamino,        di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl,        halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, unsubstituted        phenylamino or phenylamino substituted once or many times;        phenylcarbonyl which is unsubstituted or substituted once or        many times; phenyl which is unsubstituted or substituted once or        many times; phenoxy which is unsubstituted or substituted once        or many times; and pyridyloxy which is unsubstituted or        substituted once or many times, whereby the substituents may        each be independent of one another and are selected from the        group consisting of halogen, nitro, cyano, C₁-C₆-alkyl,        halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylamino,        C₃-C₆-cycloalkylthio, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio,        C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino,        di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl,        halo-C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl; or    -   unsubstituted hetaryl or hetaryl which is substituted once or        many times and is bound by a ring carbon atom, whereby the        substituents of A₁ and A₂ may be independent of one another and        are selected from the group consisting of halogen, nitro, cyano,        C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylamino,        C₃-C₆-cycloalkylthio, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio,        C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino,        di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl,        halo-C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl;    -   especially, independently of one another, aryl which is        unsubstituted or is substituted once or many times, whereby the        substituents of A₁ and A₂, independently of one another, are        selected from the group consisting of halogen, nitro, cyano,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₃-C₅-cycloalkyl, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,        C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl,        C₁-C₄-alkoxycarbonyl, unsubstituted phenyl or phenyl which is        substituted once or many times; phenoxy which is unsubstituted        or substituted once or many times; and pyridyloxy which is        unsubstituted or substituted once or many times, whereby the        substituents are each independent of one another and are        selected from the group consisting of halogen, nitro, cyano,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₃-C₅-cycloalkyl, C₃-C₅-cycloalkyloxy, C₃-C₅cycloalkylamino,        C₃-C₅-cycloalkylthio, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,        C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkylcarbonyl,        halo-C₁-C₄-alkylcarbonyl and C₁-C₄-alkoxycarbonyl; or    -   unsubstituted hetaryl or hetaryl which is substituted once or        many times and is bound by a ring carbon atom, whereby the        substituents of A₁ and A₂ may be independent of one another and        are selected from the group consisting of halogen, nitro, cyano,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₃-C₅-cycloalkyl, C₃-C₅-cycloalkyloxy, C₃-C₅-cycloalkylamino,        C₃-C₅-cycloalkylthio, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,        C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkylcarbonyl,        halo-C₁-C₄-alkylcarbonyl and C₁-C₄-alkoxycarbonyl;    -   especially, independently of one another, aryl which is        unsubstituted or is substituted once or many times, whereby the        substituents of A₁ and A₂, independently of one another, are        selected from the group consisting of halogen, nitro, cyano,        C₁-C₂-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₃-C₅-cycloalkyl, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio,        C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl,        C₁-C₂-alkoxycarbonyl, and unsubstituted phenyl or phenyl which        is substituted once or many times, whereby the substituents are        each independent of one another and are selected from the group        consisting of halogen, nitro, cyano, C₁-C₂-alkyl,        halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy,        C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyloxy, C₃-C₄-cycloalkylamino,        C₃-C₄-cycloalkylthio, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio,        C₁-C₂-alkylamino, di-C₁-C₂-alkylamino, C₁-C₂-alkylcarbonyl,        halo-C₁-C₂-alkylcarbonyl and C₁-C₂-alkoxycarbonyl;    -   (2) A compound of formula I, wherein R₁ is hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl or C₁-C₄-alkoxymethyl;    -   especially hydrogen, C₁-C₂-alkyl or halo-C₁-C₂-alkyl;    -   most particularly hydrogen or C₁-C₂-alkyl;    -   (3) A compound of formula I, wherein R₂, R₃, R₄, R₅ and R₆,        independently of one another, signify hydrogen, halogen,        unsubstituted C₁-C₄-alkyl or C₁-C₄-alkyl which is substituted        once or many times, whereby the substituents may be independent        of one another and are selected from the group consisting of        halogen and C₁-C₄-alkoxy, C₃-C₅-cycloalkyl or phenyl which is        unsubstituted or is substituted once or many times, whereby the        substituents may be independent of one another and are selected        from the group consisting of halogen, C₁-C₄-alkyl,        halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and halo-C₁-C₄-alkoxy;    -   especially, independently of one another, hydrogen,        unsubstituted C₁-C₄-alkyl or C₁-C₄-alkyl which is substituted        once or many times, whereby the substituents may be independent        of one another and are selected from the group consisting of        halogen and C₁-C₂-alkoxy; or C₃-C₅-cycloalkyl;    -   most particularly, independently of one another, hydrogen,        C₁-C₂-alkyl or C₃-C₅-cycloalkyl;    -   (4) A compound of formula I, wherein R₇ is C₁-C₆-alkyl;    -   especially C₁-C₄-alkyl;    -   most particularly C₁-C₂-alkyl;    -   (5) A compound of formula I, wherein either R₈ signifies        C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₃-C₆-cycloalkyl or        C₃-C₆-cycloalkoxy; and R_(8′) signifies hydrogen;    -   or R₈ and R_(8′) together signify unsubstituted or R₉        substituted C₃-C₄-alkylene, whereby one or two carbon atoms may        be replaced by O or N;    -   especially either R₈ signifies C₁-C₄-alkylamino,        di-C₁-C₄-alkylamino; and R_(8′) signifies hydrogen,    -   or R₈ and R_(8′) together signify unsubstituted or        R₉-substituted C₃-alkylene, whereby one or two carbon atoms may        be replaced by O;    -   most particularly either R₈ signifies C₁-C₄-alkylamino or        di-C₁-C₄-alkylamino; and R_(8′) signifies hydrogen,    -   (6) A compound of formula I, wherein R₉ signifies halogen,        nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy,        halo-C₁-C₄-alkoxy, C₂-C₅₋alkenyl, halo-C₂-C₅-alkenyl,        C₂-C₅-alkinyl, C₃-C₅-cycloalkyl, C₃-C₅-cycloalkyloxy,        C₃-C₅-cycloalkylamino, C₃-C₅-cycloalkylthio, C₂-C₅-alkenyloxy,        halo-C₂-C₅-alkenyloxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,        C₁-C₄-alkylsulfonyloxy, halo-C₁-C₄-alkylsulfonyloxy,        C₁-C₄-alkylsulfonyl, halo-C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino,        di-C₁-C₄-alkylamino, C₁-C₄-alkylcarbonyl,        halo-C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,        C₁-C₄-alkylaminocarbonyl or di-C₁-C₄-alkylaminocarbonyl;    -   especially halogen, cyano, C₁-C₃-alkyl, halo-C₃-C₃-alkyl,        C₁-C₃-alkoxy, halo-C₁-C₃-alkoxy, C₃-C₄-cycloalkyl,        C₃-C₄-cycloalkyloxy, C₃-C₄-cycloalkylamino, C₁-C₃alkylthio,        halo-C₁-C₃-alkylthio, C₁-C₃-alkylsulfonyl,        halo-C₁-C₃-alkylsulfonyl, C₁-C₃-alkylamino, di-C₁-C₃-alkylamino,        C₁-C₃-alkylcarbonyl, halo-C₁-C₃-alkylcarbonyl or        C₁-C₃-alkoxycarbonyl;    -   most particularly halogen, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl,        C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₃-C₄-cycloalkyl,        C₃-C₄-cycloalkyloxy, C₁-C₂-alkylthio or halo-C₁-C₂-alkylthio;    -   (7) A compound of formula I, wherein W is O or S;    -   especially O;    -   (8) A compound of formula I, wherein X is O or N(R₇);    -   especially O;    -   (9) A compound of formula I, wherein a is 1, 2 or 3;    -   especially 1 or 2;    -   particularly 1;    -   (10) A compound of formula I, wherein b is 0, 1 or 2;    -   especially 0 or 1;    -   particularly 0;    -   (11) A compound of formula I, wherein c is 0;    -   (12) A compound of formula I, wherein A₁ and A₂, independently        of one another, signify aryl which is unsubstituted or        substituted once or many times, whereby the substituents of A₁        and A₂, independently of one another, are selected from the        group consisting of halogen, nitro, cyano, C₁-C₆-alkyl,        halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆alkoxy,        C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy,        C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl,        halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,        C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl,        C₁-C₆-alkoxycarbonyl, unsubstituted phenylamino or phenylamino        substituted once or many times; phenylcarbonyl which is        unsubstituted or substituted once or many times; phenyl which is        unsubstituted or substituted once or many times; phenoxy which        is unsubstituted or substituted once or many times; and        pyridyloxy which is unsubstituted or substituted once or many        times, whereby the substituents may each be independent of one        another and are selected from the group consisting of halogen,        nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy,        halo-C₁-C₆-alkoxy, C₃-C₈-cycloalkyl, C₃-C₆-cycloalkyloxy,        C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkylthio, C₁-C₆-alkylthio,        halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl,        halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,        C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl and        C₁-C₆-alkoxycarbonyl; or    -   unsubstituted hetaryl or hetaryl which is substituted once or        many times and is bound by a ring carbon atom, whereby the        substituents of A₁ and A₂ may be independent of one another and        are selected from the group consisting of halogen, nitro, cyano,        C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylamino,        C₃-C₆-cycloalkylthio, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio,        C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino,        di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl,        halo-C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl;    -   R₁ signifies hydrogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl or        C₁-C₄-alkoxymethyl;    -   R₂, R₃, R₄, R₅ and R₈, independently of one another, signify        hydrogen, halogen, unsubstituted C₁-C₄-alkyl or C₁-C₄-alkyl        which is substituted once or many times, whereby the        substituents may be independent of one another and are selected        from the group consisting of halogen and C₁-C₄-alkoxy;        C₃-C₅-cycloalkyl or phenyl which is unsubstituted or is        substituted once or many times, whereby the substituents may be        independent of one another and are selected from the group        consisting of halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,        C₁-C₄-alkoxy and halo-C₁-C₄-alkoxy;    -   R₇ is C₁-C₆-alkyl;    -   either R₈ signifies C₁-C₄-alkylamino, di-C₁-C₄-alkylamino,        C₃-C₆-cycloalkyl or C₃-C₆-cycloalkoxy; and R_(8′) signifies        hydrogen;    -   or R₈ and R_(8′) together signify unsubstituted or        R₉-substituted C₃-C₄-alkylene, whereby one or two carbon atoms        may be replaced by O or N;    -   R₉ signifies halogen, nitro, cyano, C₁-C₄-alkyl,        halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₂-C₅-alkenyl, halo-C₂-C₅-alkenyl, C₂-C₆-alkinyl,        C₃-C₅-cycloalkyl, C₃-C₅-cycloalkyloxy, C₃-C₅cycloalkylamino,        C₃-C₅-cycloalkylthio, C₃-C₅-alkenyloxy, halo-C₂-C₅-alkenyloxy,        C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyloxy,        halo-C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylsulfonyl,        halo-C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino,        C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl or        di-C₁-C₄-alkylaminocarbonyl;    -   W is O or S;    -   X signifies O or N(R₇);    -   a signifies 1, 2 or 3;    -   b signifies 0, 1 or 2; and    -   c signifies 0;    -   (13) A compound of formula I, wherein A₁ and A₂, independently        of one another, signify aryl which is unsubstituted or is        substituted once or many times, whereby the substituents of A₁        and A₂, independently of one another, are selected from the        group consisting of halogen, nitro, cyano, C₁-C₄-alkyl,        halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₃-C₅-cycloalkyl, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,        C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl,        C₁-C₄-alkoxycarbonyl, unsubstituted phenyl or phenyl which is        substituted once or many times; phenoxy which is unsubstituted        or substituted once or many times; and pyridyloxy which is        unsubstituted or substituted once or many times, whereby the        substituents are each independent of one another and are        selected from the group consisting of halogen, nitro, cyano,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₃-C₅-cycloalkyl, C₃-C₅-cycloalkyloxy, C₃-C₅-cycloalkylamino,        C₃-C₅-cycloalkylthio, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,        C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkylcarbonyl,        halo-C₁-C₄-alkylcarbonyl and C₁-C₄-alkoxycarbonyl; or    -   unsubstituted hetaryl or hetaryl which is substituted once or        many times and is bound by a ring carbon atom, whereby the        substituents of A₁ and A₂ may be independent of one another and        are selected from the group consisting of halogen, nitro, cyano,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₃-C₅cycloalkyl, C₃-C₅-cycloalkyloxy, C₃-C₅-cycloalkylamino,        C₃-C₅-cycloalkylthio, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,        C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkylcarbonyl,        halo-C₁-C₄-alkylcarbonyl and C₁-C₄-alkoxycarbonyl;    -   R¹ signifies hydrogen, C₁C₂-alkyl or halo-C₁-C₂-alkyl;    -   R₂, R₃, R₄, R₅ and R₆, independently of one another, signify        hydrogen, unsubstituted C₁-C₄-alkyl or C₁-C₄-alkyl which is        substituted once or many times, whereby the substituents may be        independent of one another and are selected from the group        consisting of halogen and C₁-C₂-alkoxy; or C₃-C₅-cycloalkyl;    -   R₇ signifies C₁-C₄-alkyl;    -   either R₈ signifies C₁-C₄-alkylamino, di-C₁-C₄-alkylamino; and        R_(8′) signifies hydrogen;    -   or R₈ and R_(8′) together signify unsubstituted or        R₉-substituted C₃-alkylene, whereby one or two carbon atoms may        be replaced by O;    -   R₉ signifies halogen, cyano, C₁-C₃-alkyl, halo-C₁-C₃-alkyl,        C₁-C₃-alkoxy, halo-C₁-C₃-alkoxy, C₃-C₄-cycloalkyl,        C₃-C₄-cycloalkyloxy, C₃-C₄-cycloalkylamino, C₁-C₃-alkylthio,        halo-C₁-C₃-alkylthio, C₁-C₃-alkylsulfonyl,        halo-C₁-C₃-alkylsulfonyl, C₁-C₃-alkylamino, di-C₁-C₃-alkylamino,        C₁-C₃-alkylcarbonyl, halo-C₁-C₃-alkylcarbonyl or        C₁-C₃-alkoxycarbonyl;    -   W and X signify O;    -   a signifies 1 or 2;    -   b signifies 0 or 1; and    -   c signifies 0;    -   (14) A compound of formula I, wherein A₁ and A₂, independently        of one another, signify aryl which is unsubstituted or is        substituted once or many times, whereby the substituents of A₁        and A₂, independently of one another, are selected from the        group consisting of halogen, nitro, cyano, C₁-C₂-alkyl,        halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₃-C₅-cycloalkyl, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio,        C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl,        C₁-C₂-alkoxycarbonyl, and unsubstituted phenyl or phenyl which        is substituted once or many times, whereby the substituents may        each be independent of one another and are selected from the        group consisting of halogen, nitro, cyano, C₁-C₂-alkyl,        halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy,        C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyloxy, C₃-C₄-cycloalkylamino,        C₃-C₄-cycloalkylthio, C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio,        C₁-C₂-alkylamino, di-C₁-C₂-alkylamino, C₁-C₂-alkylcarbonyl,        halo-C₁-C₂-alkylcarbonyl and C₁-C₂-alkoxycarbonyl;    -   R₁ signifies hydrogen or C₁-C₂-alkyl;    -   R₂, R₃, R₄, R₅ and R₆, independently of one another, signify        hydrogen, C₁-C₂-alkyl or C₃-C₅-cycloalkyl;    -   R₇ signifies C₁-C₂-alkyl;    -   R₈ signifies C₁-C₄-alkylamino, di-C₁-C₄-alkylamino;    -   R_(8′) signifies hydrogen;    -   R₉ signifies halogen, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl,        C₁-C₂alkoxy, halo-C₁-C₂-alkoxy, C₃-C₄-cycloalkyl,        C₃-C₄-cycloalkyloxy, C₁-C₂-alkylthio or halo-C₁-C₂-alkylthio;    -   W and X signify O;    -   a signifies 1; and    -   b and c are 0.

Within the context of the invention, particular preference is given tothe compounds of formula I listed in Table 1, and most particularlythose named in the synthesis examples.

A further object of the invention is the process for the preparation ofthe compounds of formula I, respectively in free form or in salt form,for example characterised in that a compound of formula

which is known or may be produced analogously to corresponding knowncompounds, and wherein R₁, R₂, R₃, R₄, R₅, R₆, R₈, R_(8′), R₉, W, X, A₂,a, b and c are defined as given for formula I, is reacted with acompound of formula

which is known or may be produced analogously to corresponding knowncompounds, and wherein Ar₁ is defined as given for formula I and a is aleaving group, optionally in the presence of a basic catalyst,

-   -   and if desired, a compound of formula I obtainable according to        the method or in another way, respectively in free form or in        salt form, is converted into another compound of formula I, a        mixture of isomers obtainable according to the method is        separated and the desired isomer isolated and/or a free compound        of formula I obtainable according to the method is converted        into a salt or a salt of an compound of formula I obtainable        according to the method is converted into the free compound of        formula I or into another salt.

What has been stated above for salts of compounds I also appliesanalogously to salts of the starting materials listed hereinabove andhereinbelow.

The reaction partners can be reacted with one another as they are, i.e.without the addition of a solvent or diluent, e.g. in the melt. In mostcases, however, the addition of an inert solvent or diluent, or amixture thereof, is of advantage. Examples of such solvents or diluentsare: aromatic, aliphatic and alicyclic hydrocarbons and halogenatedhydrocarbons, such as benzene, toluene, xylene, mesitylene, tetraline,chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane,cyclohexane, dichloromethane, trichloromethane, tetrachloromethane,dichloroethane, trichloroethene or tetrachloroethene; ethers, such asdiethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether,tert-butyl methyl ether, ethylene glycol monomethyl ether, ethyleneglycol monoethyl ether, ethylene glycol dimethylether,dimethoxydlethylether, tetrahydrofuran or dioxane; ketones such asacetone, methyl ethyl ketone or methyl isobutyl ketone; amides such asN,N-dimethylformamide, N,N-diethyl-formamide, N,N-dimethylacetamide,N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles suchas acetonitrile or propionitrile; and sulfoxides, such as dimethylsulfoxide.

Preferred leaving groups Q are halogens, tosylates, mesylates andtriflates, most preferably halogens, especially chlorine.

Suitable bases for facilitating the reaction are e.g. alkali metal oralkaline earth metal hydroxides, hydrides, amides, alkanolates,acetates, carbonates, dialkylamides or alkylsilylamides; alkylamines,alkylenediamines, optionally N-alkylated, optionally unsaturated,cycloalkylamines, basic heterocycles, ammonium hydroxides, as well ascarbocyclic amines. Those which may be mentioned by way of example aresodium hydroxide, hydride, amide, methanolate, acetate, carbonate,potassium tert.-butanolate, hydroxide, carbonate, hydride, lithiumdiisopropylamide, potassium bis(trimethylsilyl)-amide, calcium hydride,triethylamine, diisopropylethylamine, triethylenedlamine,cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline,pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine,N-methylmorpholine, benzyltrimethylammonium hydroxide, as well as1,5-diazabicyclo[5.4.0]undec-5-ene (DBU). Preference is given todiisopropylethylamine and 4-(N,N-dimethylamino)pyridine.

The reaction advantageously takes place in a temperature range of ca. 0°C. to ca. 100° C., preferably from ca. 10° C. to ca. 40° C.

A further object of the invention is the process for the preparation ofthe compounds of formula II, respectively in free form or in salt form,for example characterised in that a compound of formula

which is known or may be produced analogously to corresponding knowncompounds, in which R₂, R₃, R₄, R₅, R₆, R₈, R_(8′), R₉, W, X, A₂, a, band c are defined as for formula I, is reacted with an inorganic ororganic cyanide and with a compound of formula R₁—NH₂, which is known ormay be produced analogously to corresponding known compounds and whereinR₁ is defined as for formula I, and if desired, a compound of formula IIobtainable according to the method or in another way, respectively infree form or in salt form, is converted into another compound of formulaII, a mixture of isomers obtainable according to the method is separatedand the desired isomer isolated and/or a free compound of formula IIobtainable according to the method is converted into a salt or a salt ofan compound of formula II obtainable according to the method isconverted into the free compound of formula II or into another salt.

Suitable cyanides are sodium cyanide, potassium cyanide, trimethylsilylcyanide and acetone cyanohydrin.

The general method for reacting carbonyl compounds, e.g. of formula IV,with cyanides and amines, e.g. of formula R₆—NH₂, is a Streckerreaction, for example as in Organic Synthesis Coll. Vol. 3, 88 (1973).

Salts of compounds I may be produced in known manner. Acid additionsalts of compounds I, for example, are obtainable by treatment with asuitable acid or a suitable ion exchange reagent, and salts with basesare obtainable by treatment with a suitable base or a suitable ionexchange reagent.

Salts of compounds I can be converted into the free compounds I by theusual means, acid addition salts e.g. by treating with a suitable basiccomposition or with a suitable ion exchange reagent, and salts withbases e.g. by treating with a suitable acid or a suitable ion exchangereagent.

Salts of compounds I can be converted Into other salts of compounds I ina known manner; acid addition salts can be converted for example intoother acid addition salts, e.g. by treating a salt of an inorganic acid,such as a hydrochloride, with a suitable metal salt, such as a sodium,barium, or silver salt, of an acid, e.g. with silver acetate, in asuitable solvent, in which a resulting inorganic salt, e.g. silverchloride, is insoluble and thus precipitates out from the reactionmixture.

Depending on the method and/or reaction conditions, compounds I withsalt-forming characteristics can be obtained in free form or in the formof salts.

Compounds I can also be obtained in the form of their hydrates and/oralso can include other solvents, used for example where necessary forthe crystallsation of compounds present in solid form.

The compounds I may be optionally present as optical and/or geometricisomers or as a mixture thereof. The invention relates both to the pureisomers and to all possible isomeric mixtures, and is hereinbefore andhereinafter understood as doing so, even if stereochemical details arenot specifically mentioned in every case.

Diastereoisomeric mixtures of compounds I, which are obtainable by theprocess or in another way, may be separated in known manner, on thebasis of the physical-chemical differences in their components, into thepure diastereolsomers, for example by fractional crystallisation,distillation and/or chromatography.

Splitting of mixtures of enantiomers, that are obtainable accordingly,into the pure isomers, may be achieved by known methods, for example byrecrystallisation from an optically active solvent, by chromatography onchiral adsorbents, e.g. high-pressure liquid chromatography (HPLC) onacetyl cellulose, with the assistance of appropriate micro-organisms, bycleavage with specific immobilised enzymes, through the formation ofinclusion compounds, e.g. using chiral crown ethers, whereby only oneenantiomer is complexed.

According to the invention, apart from separation of correspondingisomer mixtures, generally known methods of diastereoselective orenantioselective synthesis can also be applied to obtain purediastereoisomers or enantiomers, e.g. by carrying out the method of theinvention using educts with correspondingly suitable stereochemistry.

It is advantageous to isolate or synthesise the biologically more activeisomer, e.g. enantiomer, provided that the individual components havediffering biological efficacy.

In the method of the present invention, the starting materials andintermediates used are preferably those that lead to the compounds Idescribed at the beginning as being especially useful.

The invention relates in particular to the preparation method describedin the examples.

Starting materials and intermediates, which are new and are usedaccording to the invention for the preparation of compounds I, as wellas their usage and process for the preparation thereof, similarly forman object of the invention.

The compounds I according to the invention are notable for their broadactivity spectrum and are valuable active ingredients for use in pestcontrol, including in particular the control of endo- andecto-parasites, especially helminths, in and on warm-blooded animals,especially livestock and domestic animals, and also on plants, whilstbeing well-tolerated by warm-blooded animals, fish and plants.

In the context of the present invention, ectoparasites are understood tobe in particular insects, mites and ticks. These include insects of theorder: Lepidoptera, Coleoptera, Homoptera, Heteroptera, Diptera,Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura,Isoptera, Psocoptera and Hymenoptera. However, the ectoparasites whichmay be mentioned in particular are those which trouble humans or animalsand carry pathogens, for example flies such as Musca domestica, Muscavetustissima, Musca autumnalis, Fannia canicularis, Sarcophaga camaria,Lucilia cuprina, Hypoderma bovis, Hypoderma lineatum, Chrysomylachloropyga, Dermatobia hominis, Cochilomyla hominivorax, Gasterophilusintestinalis, Oestrus ovis, Stomoxys calcitrans, Haematobia irritans andmidges (Nematocera), such as Culicidae, Slmulildae, Psychodidae, butalso blood-sucking parasites, for example fleas, such as Ctenocephalidesfelis and Ctenocephalides canis (cat and dog fleas), Xenopsylla cheopis,Pulex irritans, Dermatophilus penetrans, lice, such as Damalina ovis,Pediculus humanis, biting flies and horseflies (Tabanidae), Haematopotaspp. such as Haematopota pluvialis, Tabanidea spp. such as Tabanusnigrovittatus, Chrysopsinae spp. such as Chrysops caecutiens, tsetseflies, such as species of Glossinia, biting insects, particularlycockroaches, such as Blatella germanica, Blaffa orientalls, Periplanetaamericana, mites, such as Dermanyssus galilnae, Sarcoptes scabiel,Psoroptes ovis and Psorergates spp. and last but not least ticks. Thelatter belong to the order Acarina. Known representatives of ticks are,for example, Boophilus, Amblyomma, Anocentor, Dermacentor,Haemaphysalls, Hyalomma, Ixodes, Rhipicentor, Margaropus, Rhipicephalus,Argas, Otoblus and Omithodoros and the like, which preferably infestwarm-blooded animals including farm animals, such as cattle, pigs, sheepand goats, poultry such as chickens, turkeys and geese, fur-bearinganimals such as mink, foxes, chinchillas, rabbits and the like, as wellas domestic animals such as cats and dogs, but also humans.

The compounds I according to the invention are also active against allor individual development stages of animal pests showing normalsensitivity, as well as those showing resistance, such as insects andmembers of the order Acarina. The insecticidal, ovicidal and/oracariddal effect of the active substances of the invention can manifestitself directly, i.e. killing the pests either immediately or after sometime has elapsed, for example when moulting occurs, or by destroyingtheir eggs, or indirectly, e.g. reducing the number of eggs laid and/orthe hatching rate, good efficacy corresponding to a pesticidal rate(mortality) of at least 50 to 60%.

Compounds I can also be used against hygiene pests, especially of theorder Diptera of the families Sarcophagidae, Anophilidae and Culicidae;the orders Orthoptera, Dictyoptera (e.g. the family Blatildae) andHymenoptera (e.g. the family Formicidae).

Compounds I also have sustainable efficacy on parasitic mites andinsects of plants. In the case of spider mites of the order Acarina,they are effective against eggs, nymphs and adults of Tetranychidae(Tetranychus spp. and Panonychus spp.).

They have high activity against sucking insects of the order Homoptera,especially against pests of the families Aphididae, Delphacidae,Cicadellidae, Psyllidae, Loccidae, Diaspididae and Erlophydidae (e.g.rust mite on citrus fruits); the orders Hemiptera, Heteroptera andThysanoptera, and on the plant-eating insects of the orders Lepidoptera,Coleoptera, Diptera and Orthoptera.

They are similarly suitable as a soil insecticide against pests in thesoil.

The compounds of formula I are therefore effective against all stages ofdevelopment of sucking insects and eating insects on crops such ascereals, cotton, rice, maize, soya, potatoes, vegetables, fruit,tobacco, hops, citrus, avocados and other crops.

The compounds of formula I are also effective against plant nematodes ofthe species Meloidogyne, Heterodera, Pratylenchus, Dityienchus,Radopholus, Rizoglyphus etc.

In particular, the compounds are effective against helminths, in whichthe endoparasitic nematodes and trematodes may be the cause of seriousdiseases of mammals and poultry, e.g. sheep, pigs, goats, cattle,horses, donkeys, dogs, cats, guinea-pigs and exotic birds. Typicalnematodes of this indication are: Haemonchus, Trichostrongylus,Ostertagia, Nematodinrs, Cooperda, Ascarls, Bunostonum, Oesophagostonum,Charbertla, Tdichuds, Strongylus, Tdchonema, Dictyocaulus, Capillaria,Heteraids, Toxocara, Ascarddla, Oxyuris, Ancylostoma, Uncinada,Toxascards and Parascadis. The trematodes include, in particular, thefamily of Fasclolideae, especially Fasciola hepatica. It could also beshown surprisingly and unexpectedly that the compounds of formula I haveexceptionally high efficacy against nematodes that are resistant to manyactive substances. This can be demonstrated in vito by the LDA test andin vivo for example in Mongolian gerbils and sheep. It was shown thatamounts of active substance which kill sensitive strains of Haemonchuscontortus or Trichostrongylus colubriformis, are also sufficientlyeffective at controlling corresponding strains that are resistant tobenzimidazoles, levamisol and macrocyclic lactones (for exampleivermectin).

Certain pests of the species Nematodirus, Cooperia and Oesophagostonuminfest the intestinal tract of the host animal, while others of thespecies Haemonchus and Ostertagia are parasitic in the stomach and thoseof the species Dictyocaulus are parasitic in the lung tissue. Parasitesof the families Filariidae and Setariidae may be found in the internalcell issue and in the organs, e.g. the heart, the blood vessels, thelymph vessels and the subcutaneous tissue. A particularly notableparasite is the heartworm of the dog, Dirofilaria immitis. The compoundsof formula I are highly effective against these parasites.

The pests which may be controlled by the compounds of formula I alsoinclude those from the class of Cestoda (tapeworms), e.g. the familiesMesocestoidae, especially of the genus Mesocestoides, in particular M.lineatus; Dilepidide, especially Dipylidium caninum, Joyeuxiella spp.,in particular Joyeuxiella pasquali, and Diplopylidium spp., andTaeniidae, especially Taenia pisiformis, Taenia ceryl, Taenia ovis,Taneia hydatigena, Taenia multiceps, Taenia taenlaeformis, Taeniaserialis, and Echinocuccus spp., most preferably Taneia hydatigena,Taenia ovis, Taenia multiceps, Taenia seralis; Echinocuccus granulosusand Echinococcus granulosus and Echinococcus multilocularis, as well asMulticeps multiceps.

Most particularly, Taenla hydatigena, T. pisiformis, T. ovis, T.taenlaefornis, Multiceps multiceps, Joyeuxiella pasquali, Dipylidiumcaninum, Mesocestoides spp., Echinococcus granulosus and E.multiloculadis are controlled on or in dogs and cats simultaneously withDirofilaria immills, Ancylostoma ssp., Toxocara ssp. and/or Trichurdsvulpis. Equally preferred, Ctenocephalides felis and/or C. canis aresimultaneously controlled with the above-mentioned nematodes andcestodes.

Furthermore, the compounds of formula I are suitable for the control ofhuman pathogenic parasites. Of these, typical representatives thatappear in the digestive tract are those of the species Ancylostoma,Necator, Ascarls, Strongyloldes, Trichinella, Capillaria, Trichurds andEnterobius. The compounds of the present invention are also effectiveagainst parasites of the species Wuchereria, Brugia, Onchocerca and Loafrom the family of Filaridae, which appear in the blood, in the tissueand in various organs, and also against Dracunculus and parasites of thespecies Strongyloldes and Trichinella, which infect the gastrointestinaltract in particular.

In addition, the compounds of formula I are also effective againstharmful and pathogenic fungi on plants, as well as on humans andanimals.

The good pesticidal activity of the compounds of formula I according tothe invention corresponds to a mortality rate of at least 50-60% of thepests mentioned. In particular, the compounds of formula I are notablefor the exceptionally long duration of efficacy.

The compounds of formula I are preferably employed in unmodified form orpreferably together with the adjuvants conventionally used in the art offormulation and may therefore be processed in a known manner to give,for example, emulsifiable concentrates, directly dilutable solutions,dilute emulsions, soluble powders, granules or microencapsulations inpolymeric substances. As with the compositions, the methods ofapplication are selected in accordance with the intended objectives andthe prevailing circumstances.

The formulation, i.e. the agents, preparations or compositionscontaining the active ingredient of formula I, or combinations of theseactive ingredients with other active ingredients, and optionally a solidor liquid adjuvant, are produced in a manner known per se, for exampleby intimately mixing and/or grinding the active ingredients withspreading compositions, for example with solvents, solid carriers, andoptionally surface-active compounds (surfactants).

The solvents in question may be: alcohols, such as ethanol, propanol orbutanol, and glycols and their ethers and esters, such as propyleneglycol, dipropylene glycol ether, ethylene glycol, ethylene glycolmonomethyl or -ethyl ether, ketones, such as cyclohexanone, isophoroneor diacetanol alcohol, strong polar solvents, such asN-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, orwater, vegetable oils, such as rape, castor, coconut, or soybean oil,and also, if appropriate, silicone oils.

Preferred application forms for usage on warm-blooded animals in thecontrol of helminths include solutions, emulsions, suspensions(drenches), food additives, powders, tablets including effervescenttablets, boll, capsules, micro-capsules and pour-on formulations,whereby the physiological compatibility of the formulation excipientsmust be taken into consideration.

The binders for tablets and boll may be chemically modified polymericnatural substances that are soluble in water or in alcohol, such asstarch, cellulose or protein derivatives (e.g. methyl cellulose,carboxymethyl cellulose, ethylhydroxyethyl cellulose, proteins such aszein, gelatin and the like), as well as synthetic polymers, such aspolyvinyl alcohol, polyvinyl pyrrolidone etc. The tablets also containfillers (e.g. starch, microcrystalline cellulose, sugar, lactose etc.),glidants and disintegrants.

If the anthelminthics are present in the form of feed concentrates, thenthe carriers used are e.g. performance feeds, feed grain or proteinconcentrates. Such feed concentrates or compositions may contain, apartfrom the active ingredients, also additives, vitamins, antibiotics,chemotherapeutics or other pesticides, primarily bacteriostats,fungistats, coccidiostats, or even hormone preparations, substanceshaving anabolic action or substances which promote growth, which affectthe quality of meat of animals for slaughter or which are beneficial tothe organism in another way. If the compositions or the activeingredients of formula I contained therein are added directly to feed orto the drinking troughs, then the formulated feed or drink contains theactive ingredients preferably in a concentration of ca. 0.0005 to 0.02%by weight (5-200 ppm).

The compounds of formula I according to the invention may be used aloneor in combination with other biocides. They may be combined withpesticides having the same sphere of activity e.g. to increase activity,or with substances having another sphere of activity e.g. to broaden therange of activity. It can also be sensible to add so-called repellents.If the range of activity is to be extended to endoparasites, e.g.wormers, the compounds of formula I are suitably combined withsubstances having endoparasiuc properties. Of course, they can also beused in combination with antibacterial compositions. Since the compoundsof formula I are adulticides, i.e. since they are effective inparticular against the adult stage of the target parasites, the additionof pesticides which instead attack the juvenile stages of the parasitesmay be very advantageous. In this way, the greatest part of thoseparasites that produce great economic damage will be covered. Moreover,this action will contribute substantially to avoiding the formation ofresistance. Many combinations may also lead to synergistic effects, i.e.the total amount of active ingredient can be reduced, which is desirablefrom an ecological point of view. Preferred groups of combinationpartners and especially preferred combination partners are named in thefollowing, whereby combinations may contain one or more of thesepartners in addition to a compound of formula I.

Suitable partners in the mixture may be blocides, e.g. the insecticidesand acariddes with a varying mechanism of activity, which are named inthe following and have been known to the person skilled in the art for along time, e.g. chitin synthesis inhibitors, growth regulators; activeingredients which act as juvenile hormones; active ingredients which actas adulticides; broad-band insecticides, broad-band acariddes andnematicides; and also the well known anthelminthics and insect- and/oracarid-deterring substances, said repellents or detachers.

Non-limitative examples of suitable insecticides and acaricides are: 1.Abamectin 2. AC 303 630 3. Acephat 4. Acrinathrin 5. Alanycarb 6.Aldicarb 7. α-Cypermethrin 8. Alphamethrin 9. Amitraz 10. Avermectin B₁11. AZ 60541 12. Azinphos A 13. Azinphos M 14. Azocyclotin 15. Bacillussubtil. toxin 16. Bendiocarb 17. Benfuracarb 18. Bensultap 19.β-Cyfluthrin 20. Bifenthrin 21. BPMC 22. Brofenprox 23. Bromophos A 24.Bufencarb 25. Buprofezin 26. Butocarboxim 27. Butylpyridaben 28.Cadusafos 29. Carbaryl 30. Carbofuran 31. Carbophenothion 32. Cartap 33.Cloethocarb 34. Chlorethoxyfos 35. Chlorfenapyr 36. Chlorfluazuron 37.Chlormephos 38. Chlorpyrifos 39. Cis-Resmethrin 40. Clocythrin 41.Clofentezin 42. Cyanophos 43. Cycloprothrin 44. Cyfluthrin 45. Cyhexatin46. D 2341 47. Deltamethrin 48. Demeton M 49. Demeton S 50.Demeton-S-methyl 51. Dichlofenthion 52. Dicliphos 53. Diethion 54.Diflubenzuron 55. Dimethoat 56. Dimethylvinphos 57. Dioxathion 58.DPX-MP062 59. Edifenphos 60. Emamectin 61. Endosulfan 62. Esfenvalerat63. Ethiofencarb 64. Ethion 65. Ethofenprox 66. Ethoprophos 67. Etrimfos68. Fenamiphos 69. Fenazaquin 70. Fenbutatinoxid 71. Fenitrothion 72.Fenobucarb 73. Fenothiocarb 74. Fenoxycarb 75. Fenpropathrin 76.Fenpyrad 77. Fenpyroximate 78. Fenthion 79. Fenvalerate 80. Fipronil 81.Fluazinam 82. Fluazuron 83. Flucycloxuron 84. Flucythrinat 85.Flufenoxuron 86. Flufenprox 87. Fonofos 88. Formothion 89. Fosthiazat90. Fubfenprox 91. HCH 92. Heptenophos 93. Hexaflumuron 94. Hexythiazox95. Hydroprene 98. Imidacloprid 97. insect-active fungi 98.insect-active nematodes 99. insect-active viruses 100. Iprobenfos 101.Isofenphos 102. Isoprocarb 103. Isoxathion 104. Ivermectin 105.λ-Cyhalothrin 106. Lufenuron 107. Malathion 108. Mecarbam 109.Mesulfenfos 110. Metaldehyde 111. Methamidophos 112. Methiocarb 113.Methomyl 114. Methoprene 115. Metolcarb 116. Mevinphos 117. Milbemectin118. Moxidectin 119. Naled 120. NC 184 121. NI-25, Acetamiprid 122.Nitenpyram 123. Omethoat 124. Oxamyl 125. Oxydemeton M 126. Oxydeprofos127. Parathion 128. Parathion-methyl 129. Permethrin 130. Phenthoat 131.Phorat 132. Phosalone 133. Phosmet 134. Phoxim 135. Pirimicarb 136.Pirimiphos A 137. Pirimiphos M 138. Promecarb 139. Propaphos 140.Propoxur 141. Prothiofos 142. Prothoat 143. Pyrachlofos 144.Pyradaphenthion 145. Pyresmethrin 146. Pyrethrum 147. Pyridaben 148.Pyrimidifen 149. Pyriproxyfen 150. RH 5992 151. RH-2485 152. Salithion153. Sebufos 154. Silafluofen 155. Spinosad 156. Sulfotep 157. Sulprofos158. Tebufenozide 159. Tebufenpyrad 160. Tebupirimfos 161. Teflubenzuron162. Tefluthrin 163. Temephos 164. Terbam 165. Terbufos 166.Tetrachlorvinphos 167. Thiafenox 168. Thiodicarb 169. Thiofanox 170.Thionazin 171. Thuringiensin 172. Tralomethrin 173. Triarathene 174.Triazamate 175. Triazophos 176. Triazuron 177. Trichlorfon 178.Triflumuron 179. Trimethacarb 180. Vamidothion 181. XMC (3.5,-Xylyl-methylcarbamate) 182. Xylylcarb 183. YI 5301/5302 184. ζ-Cypermethrin185. Zetamethrin

Non-limitative examples of suitable anthelminthics are named in thefollowing, a few representatives have insecticidal and acaricidalactivity in addition to the anthelminthic activity, and are partlyalready in the above list.

-   (A1)    Praziquantel=2-cydohexylcarbonyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1    -α]isoquinoline-   (A2)    Closantel=3,5-dilodo-N-[5-chloro-2-methyl-4-(a-cyano-4-chlorobenzyl)phenyl]-salicylamide-   (A3)    Triciabendazole=5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole-   (A4)    Levamisol=L-(−)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1b]thiazole-   (A5) Mebendazole=(5-benzoyl-1H-benzimidazol-2-yl)carbaminic acid    methylester-   (A6) Omphalotin=a macrocyclic fermentation product of the fungus    Omphalotus olearius described in WO 97/20857-   (A7) Abamectin=avermectin B1-   (A8) Ivermectin=22,23-dihydroavermectin B1-   (A9)    Moxidectin=5-O-demethyl-28-deoxy-25-(1,3-dimethyl-i-butenyl)-6,28    epoxy-23-(methoxyimino)-milbemycin B    -   (A10)        Doramectin=25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)-avermectin        A1a    -   (A11) Milbemectin=mixture of milbemycin A3 and milbemycin A4    -   (A12) Milbemyinoxim=5-oxime of milbemectin

Non-limitative examples of suitable repellents and detachers are:

-   -   (R1) DEET (N,N-diethyl-m-toluamide)    -   (R2) KBR 3023 N-butyl-2-oxycarbonyl-(2-hydroxy)-piperidine    -   (R3)        Cymiazole=N,-2,3-dihydro-3-methyl-1,3-thiazol-2-yldene-2,4-xylidene.

The said partners in the mixture are best known to specialists in thisfield. Most are described in various editions of the Pesticide Manual,The British Crop Protection Council, London, and others in the variouseditions of The Merck Index, Merck & Co., inc., Rahway, N.J., USA or inpatent literature. Therefore, the following listing is restricted to afew places where they may be found by way of example.

-   (I) 2-Methyl-2-(methylthio)proplonaldehyde-O-methylcarbamoyloxime    (Aldicarb), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 26;-   (II)    S-(3,4dihydro-4-oxobenzo[o]-[1,2,3]-triazinylmethyl)O,O-dimethyl-phosphorodithloate    (Azinphos-methyl), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 67;-   (III)    Ethyl-N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl-(methyl)aminothio]-N-isopropyl-β-alaninate    (Benfuracarb), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 96;-   (IV)    2-Methylbiphenyl-3-ylmethyl-(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate    (Bifenthrin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 118;-   (V) 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazian-4-one    (Buprofezin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 157;-   (VI) 2,3-Dihydro-2,2-dimethylbenzofuran-7-yl-methylcarbamate    (Carbofuran), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 186;-   (VII)    2,3-Dihydro-2,2-dimethylbenzofuran-7-yl-(dibutylaminothio)methylcarbamate    (Carbosulfan), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 188;-   (VIII) S,S′-(2-dimethylaminotrimethylene)-bis(thiocarbamate)    (Cartap), from The Pesticide Manual, 11^(th)Ed. (1997), The British    Crop Protection Council, London, page 193;-   (IX)    1-[3,5-Dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluoro-benzoyl)-urea    (Chlorofluazuron), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 213;-   (X) O,O-diethyl-O-3,5,6-trichloro-2-pyridyl-phosphorothioate    (Chlorpyrifos), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 235;-   (XI)    (RS)-α-cyano-4-fluoro-3-phenoxybenzyl-(1RS,3RS;1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-di-methylcyclopropanecarboxylate    (Cyfluthrin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 293;-   (XII) Mixture of    (S)-α-cyano-3-phenoxybenzyl-(2)-(1R,3R)-3-(2-chloro-3,3,3-trifluoro-propenyl)-2,2-dimethylcyclopropanecarboxylate    and    (R)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate    (Lambda-Cyhalothrin), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 300;-   (XIII) Racemate consisting of    (S)-α-cyano-3-phenoxybenzyl-(2)-(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    and    (R)-α-cyano-3-phenoxybenzyl-(1S,3S)3(2,2-dichlorovinyl)-2,2-dimethylcydopropanecarboxylate    (Alpha-cypermethrin), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 308;-   (XIV) a mixture of the stereoisomers of (S)-α-cyano-3-phenoxybenzyl    (1RS,3RS,-1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    (zeta-Cypermethrin), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 314;-   (XV)    (S)-α-cyano-3-phenoxybenzyl-(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate    (Deltamethrin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 344;-   (XVI) (4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (Diflubenzuron),    from The Pesticide Manual, 11^(th)Ed. (1997), The British Crop    Protection Council, London, page 395;-   (XVII)    (1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-en-2,3-ylenebismethylene)-sulphite    (Endosulfan), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 459;-   (XVIII) α-ethylthio-o-tolyl-methylcarbamate (Ethiofencarb), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 479;-   (XIX) O,O-dimethyl-O-4-nitro-m-tolyl-phosphorothioate    (Fenitrothion), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 514;-   (XX) 2-sec-butylphenyl-methylcarbamate (Fenobucarb), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 516;-   (XXI)    (RS)-α-cyano-3-phenoxybenzyl-(RS)-2-(4-chlorophenyl)-3-methylbutyrate    (Fenvalerate), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 539;-   (XXII)    S[formyl(methyl)carbamoylmethyl]-O,O-dimethyl-phosphorodithioate    (Formothion), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 625;-   (XXIII) 4-Methylthio-3,5-xylyl-methylcarbamate (Methlocarb), from    The Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 813;-   (XXIV) 7-Chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl-dimethylphosphate    (Heptenophos), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 670;-   (XXV) 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylidenamine    (Imidadoprid), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 706;-   (XXVI) 2-isopropylphenyl-methylcarbamate (isoprocarb), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 729;-   (XXVII) O,S-dimethyl-phosphoramidothioate (Methamidophos), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 808;-   (XXVII) S-Methyl-N-(methylcarbamoyloxy)thioacetimidate (Methomyl),    from The Pestidde Manual, 11^(th)Ed. (1997), The British Crop    Protection Council, London, page 815;-   (XXIX) Methyl-3-(dimethoxyphosphinoyioxy)but-2-enoate (Mevinphos),    from The Pesticide Manual, 11^(th)Ed. (1997), The British Crop    Protection Council, London, page 844;-   (XX) O,O-diethyl-O-4-nitrophenyl-phosphorothioate (Parathion), from    The Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 926;-   (XXXI) O,O-dimethyl-O-4-nitrophenyl-phosphorothioate    (Parathion-methyl), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 928;-   (XXXII)    S-6-chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl-O,O-diethyl-phosphordithioate    (Phosalone), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 963;-   (XXXIII)    2-Dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethylcarbamate    (Pirimicarb), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 985;-   (XXXIV) 2-isopropoxyphenyl-methylcarbamate (Propoxur), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 1036;-   (XXXV) 1-(3,5dichloro-2,4difluorophenyl)-3-(2,6-difluorobenzoyl)urea    (Teflubenzuron), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1158;-   (XXXVI) S-tert-butylthiomethyl-O,O-dimethyl-phosphorodithioate    (Terbufos), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1165;-   (XXXVII)    ethyl-(3-tert.-butyl-1-dimethylcarbamoyl-1H-1,2,4-triazol-5-yl-thio)-acetate,    (Triazamate), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1224;-   (XXXVIII) Abamectin, from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 3;-   (XXXIX) 2-sebutylphenyl-methylcarbamate (Fenobucarb), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 516;-   (XL) N-tert.-butyl-N-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide    (Tebufenozide), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1147;-   (XLI)    (±)-5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethyl-sulphinylpyrazol-3-carbonitrile    (Fipronil), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 545;-   (XLII)    (RS)-α-cyano-4-fluoro-3-phenoxybenzyl(1RS,3RS;1RS,3RS)3-(2,2-dichloro-vinyl)-2,2-dimethylcyclopropanecarboxylate    (beta-Cyfluthrin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 295;-   (XLIII)    (4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl)propyl](dimethyl)silane    (Silafluofen), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1105;-   (XLIV) tert.-butyl    (E)-α-(1,3-dimethyl-5-phenoxypyrazol-4-yl-methylenamino-oxy)-p-toluate    (Fenpyroximate), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 530;-   (XLV)    2-tert.-butyl-5-(4-tert.-butylbenzylthio)-4-chloropyridazin-3(2H)-one    (Pyridaben), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1161;-   (XLVI) 4-[4-(1,1-dimethylphenyl)phenyl]ethoxy]quinazoline    (Fenazaquin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 507;-   (XLVII) 4-phenoxyphenyl-(RS)-2-(pyridyloxy)propyl-ether    (Pyriproxyfen), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1073;-   (XLVIII)    5-chloro-N-{2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxylethyl)-6-ethylpyrimidine-4-amine    (Pyrimidifen), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1070;-   (XLIX)    (E)-N-(6-chloro-3pyridylmethyl)-N-ethyl-N-methyl-2-nitrovinylidenediamine    (Nitenpyram), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 880;-   (L)    (E)-N¹-[(6-chloro-3-pyridyl)methyl]-N²-cyano-N¹-methylacetamidine    (NI-25, Acetamiprid), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 9;-   (LI) Avermectin B₁, from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 3;-   (LII) an insect-active extract from a plant, especially    (2R,6aS,12aS)-1,2,6,6a,12,12a-hexhydro-2-isopropenyl-8,9-dimethoxychromeno[3,4-b]furo[2,3-h]chromen-6-one    (Rotenone), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1097; and an extract    from Azadirachta indica, especially azadirachtin, from The Pesticide    Manual, 11^(th)Ed. (1997), The British Crop Protection Council,    London, page 59; and-   (LIII) a preparation which contains insect-active nematodes,    preferably Heterorhabditis bactediophora and Heterorhabditis    megidis, from The Pesticide Manual, 11^(th)Ed. (1997), The British    Crop Protection Council, London, page 671; Steinemema feltiae, from    The Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 1115 and Steinernema scaptertsci, from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 1116;-   (LIV) a preparation obtainable from Bacillus subtillis, from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 72; or from a strain of Bacillus thuringiensis    with the exception of compounds isolated from GC91 or from    NCTC11821; The Pesticide Manual, 11^(th)Ed. (1997), The British Crop    Protection Council, London, page 73;-   (LV) a preparation which contains insect-active fungi, preferably    Verticillium lecanli, from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 1266; Beauveria    brogniartii, from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 85 and Beauveria    bassiana, from The Pesticide Manual, 11^(th)Ed. (1997), The British    Crop Protection Council, London, page 83;-   (LVI) a preparation which contains insect-active viruses, preferably    Neodipridon Sertifer NPV, from The Pesticide Manual, 11^(th)Ed.    (1997), The British Crop Protection Council, London, page 1342;    Mamestra brassicae NPV, from The Pesticide Manual, 11^(th)Ed.    (1997), The British Crop Protection Council, London, page 759 and    Cydia pomonella granulosis virus, from The Pesticide Manual,    11^(th)Ed. (1997), The British Crop Protection Council, London, page    291;-   (CLXXXI)    7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)-carbamoyl]indol[1,2e]oxazoline-4a-carboxylate    (DPX-MP062, Indoxycarb), from The Pesticide Manual, 11^(th)Ed.    (1997), The British Crop Protection Council, London, page 453;-   (CLXXXII)    N-tert.-butyl-N′-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide    (RH-2485, Methoxyfenozide), from The Pesticide Manual, 11^(th)Ed.    (1997), The British Crop Protection Council, London, page 1094; and-   (CLXXXIII) (N′-[4-methoxy-biphenyl-3-yl]-hydrazinecarboxylic acid    isopropylester (D 2341), from Brighton Crop Protection Conference,    1996, 487- 493;-   (R2) Book of Abstracts, 212th ACS National Meeting Orlando, Fla.,    Aug. 25-29 (1996), AGRO-020. Publisher: American Chemical Society,    Washington, D.C. CONEN: 63BFAF.

As a consequence of the above details, a further essential aspect of thepresent invention relates to combination preparations for the control ofparasites on warm-blooded animals, characterised in that they contain,in addition to a compound of formula I, at least one further activeingredient having the same or different sphere of activity and at leastone physiologically acceptable carrier. The present invention is notrestricted to two-fold combinations.

As a rule, the anthelminthic compositions according to the inventioncontain 0.1 to 99% by weight, especially 0.1 to 95% by weight of activeingredient of formula I, Ia or mixtures thereof, 99.9 to 1% by weight,especially 99.8 to 5% by weight of a solid or liquid admixture,including 0 to 25% by weight, especially 0.1 to 25% by weight of asurfactant.

Application of the compositions according to the invention to theanimals to be treated may take place topically, perorally, parenterallyor subcutaneously, the composition being present in the form ofsolutions, emulsions, suspensions, (drenches), powders, tablets, boll,capsules and pour-on formulations.

The pour-on or spot-on method consists in applying the compound offormula I to a specific location of the skin or coat, advantageously tothe neck or backbone of the animal. This takes place e.g. by applying aswab or spray of the pour-on or spot-on formulation to a relativelysmall area of the coat, from where the active substance is dispersedalmost automatically over wide areas of the fur owing to the spreadingnature of the components in the formulation and assisted by the animal'smovements.

Pour-on or spot-on formulations suitably contain carriers, which promoterapid dispersement over the skin surface or in the coat of the hostanimal, and are generally regarded as spreading oils. Suitable carriersare e.g. oily solutions; alcoholic and isopropanolic solutions such assolutions of 2-octyldodecanol or oleyl alcohol; solutions in esters ofmonocarboxylic acids, such as isopropyl myristate, isopropyl palmitate,lauric add oxalate, oleic acid oleyl ester, oleic acid decyl ester,hexyl laurate, oleyl oleate, decyl oleate, capric acid esters ofsaturated fat alcohols of chain length C₁₂-C₁₈; solutions of esters ofdicarboxylic adds, such as dibutyl phthalate, dilsopropyl isophthalate,adipic acid dilsopropyl ester, di-n-butyl adipate or also solutions ofesters of aliphatic acids, e.g. glycols. It may be advantageous for adispersing agent to be additionally present, such as one known from thepharmaceutical or cosmetic industry. Examples are 2-pyrrolidone,2-(N-alkyl)pyrrolidone, acetone, polyethylene glycol and the ethers andesters thereof, propylene glycol or synthetic triglycerides.

The oily solutions include e.g. vegetable oils such as olive oil,groundnut oil, sesame oil, pine oil, linseed oil or castor oil. Thevegetable oils may also be present in epoxidised form. Paraffins andsilicone oils may also be used.

A pour-on or spot-on formulation generally contains 1 to 20% by weightof a compound of formula I, 0.1 to 50% by weight of dispersing agent and45 to 98.9% by weight of solvent.

The pour-on or spot-on method is especially advantageous for use on herdanimals such as cattle, horses, sheep or pigs, in which it is difficultor time-consuming to treat all the animals orally or by injection.Because of its simplicity, this method can of course also be used forall other animals, including individual domestic animals or pets, and isgreatly favoured by the keepers of the animals, as it can often becarried out without the specialist presence of the veterinarian.

Whereas it is preferred to formulate commercial products asconcentrates, the end user will normally use dilute formulations.

Such compositions may also contain further additives, such asstabilisers, anti-foaming agents, viscosity regulators, binding agentsor tackifiers, as well as other active ingredients, in order to achievespecial effects.

Anthelminthic compositions of this type, which are used by the end user,similarly form a constituent of the present invention.

In each of the processes according to the invention for pest control orin each of the pest control compositions according to the invention, theactive ingredients of formula I can be used in all of their stericconfigurations or in mixtures thereof.

The invention also includes a method of prophylactically protectingwarm-blooded animals, especially productive livestock, domestic animalsand pets, against parasitic helminths, which is characterised in thatthe active ingredients of the formula or the active ingredientformulations prepared therefrom are administered to the animals as anadditive to the feed, or to the drinks or also in solid or liquid form,orally or by injection or parenteraily. The invention also includes thecompounds of formula I according to the invention for usage in one ofthe said processes.

The following examples serve merely to illustrate the invention withoutrestricting it, the term active ingredient representing a substancelisted in table 1.

In particular, preferred formulations are made up as follows:

-   -   (%=percent by weight)

FORMULATION EXAMPLES

1. Granulate a) b) active ingredient 5% 10% kaolin 94%  — highlydispersed silicic acid 1% — attapulgite — 90%

The active ingredient is dissolved in methylene chloride, sprayed ontothe carrier and the solvent subsequently concentrated by evaporationunder vacuum. Granulates of this kind can be mixed with the animal feed.2. Granulate active ingredient 3% polyethylene glycol (mw 200) 3% kaolin94% (mw = molecular weight)

The finely ground active ingredient is evenly applied in a mixer to thekaolin which has been moistened with polyethylene glycol. In this way,dust-free coated granules are obtained. 3. Tablets or boli I activeingredient 33.00% methylcellulose 0.80% silicic acid, highly dispersed0.80% corn starch 8.40% II lactose, cryst. 22.50% corn starch 17.00%microcryst. cellulose 16.50% magnesium stearate 1.00%

-   I Methyl cellulose is stirred into water. After the material has    swollen, sillicic add is stirred in and the mixture homogeneously    suspended. The active ingredient and the corn starch are mixed. The    aqueous suspension is worked into this mixture and kneaded to a    dough. The resulting mass is granulated through a 12 M sieve and    dried.-   II All 4 excipients are mixed thoroughly.

III The preliminary mixes obtained according to I and II are mixed andpressed into tablets or boll. 4. Injectables A. Oily vehicle (slowrelease) 1. active ingredient 0.1-1.0 g groundnut oil ad 100 ml 2.active ingredient 0.1-1.0 g sesame oil ad 100 ml

Preparation: The active ingredient is dissolved in part of the oilwhilst stirring and, if required, with gentle heating, then aftercooling made up to the desired volume and sterile-filtered through asuitable membrane filter with a pore size of 0.22 μm. B. Water-misciblesolvent (average rate of release) active ingredient 0.1-1.0 g4-hydroxymethyl-1,3-dioxolane (glycerol formal) 40 g 1,2-propanediol ad100 ml active ingredient 0.1-1.0 g glycerol dimethyl ketal 40 g1,2-propanediol ad 100 ml

Preparation: The active ingredient is dissolved in part of the solventwhilst stirring, made up to the desired volume and sterile-filteredthrough a suitable membrane filter with a pore size of 0.22 μm. C.Aqueous solubilisate (rapid release) 1. active Ingredient 0.1-1.0 gpolyethoxylated castor oil (40 ethylene oxide units) 10 g1,2-propanediol 20 g benzyl alcohol 1 g aqua ad Inject, ad 100 ml 2.active ingredient 0.1-1.0 g polyethoxylated sorbitan monooleate (20ethylene 8 g oxide units) 4-hydroxymethyl-1,3-dioxolane (glycerolformal) 20 g benzyl alcohol 1 g aqua ad inject, ad 100 ml

Preparation: The active ingredient is dissolved in the solvents and thesurfactant, and made up with water to the desired volume. Sterilefiltration through an appropriate membrane filter of 0.22 μm pore size.5. Pour on A. active ingredient 5 g isopropyl myristate 10 g isopropanolad 100 ml B active ingredient 2 g hexyl laurate 5 g medium-chainedtriglyceride 15 g ethanol ad 100 ml C. active ingredient 2 g oleyloleate 5 g N-methyl-pyrrolidone 40 g isopropanol ad 100 ml

The aqueous systems may also preferably be used for oral and/orintraruminal application.

The compositions may also contain further additives, such asstabilisers, e.g. where appropriate epoxidised vegetable oils(epoxidised coconut oil, rapeseed oil, or soybean oil); antifoams, e.g.silicone oil, preservatives, viscosity regulators, binders, tackifiers,as well as fertilisers or other active ingredients to achieve specialeffects.

Further biologically active substances or additives, which are neutraltowards the compounds of formula I and do not have a harmful effect onthe host animal to be treated, as well as mineral salts or vitamins, mayalso be added to the described compositions.

The following examples serve to illustrate the invention. They do notlimit the invention. The letter ‘h’ stands for hour.

PREPARATION EXAMPLES Example 1N-[2-cyano-1-(4.5-difluoro-4′-dimethylamino-2-biphenoxy)-2-propyl]-4-trifluoromethoxybenzamide

a) 2.5 g of chloroacetone, 3 g of potassium carbonate and 0.3 g ofpotassium iodide are added to 4 g of 2-bromo-4,5-difluorophenol in 40 mlof acetone, and stirred for 3 h at room temperature. After filtration,the solution is concentrated by evaporation, whereby1-(2-bromo-4,5-difluorophenoxy)-prop-2-one is obtained as a crudeproduct, which is further processed without further purification.

b) 5.1 g of 1-(2-bromo-4,5-difluorophenoxy)-propan-2-one, 1.1 g ofsodium cyanide and 1.5 g of ammonium chloride are added to 19 ml of a25% ammoniacal aqueous solution, and stirred over night at roomtemperature. Afterwards, the reaction mixture is extracted with ethylacetate, the organic phase is washed with water and brine and dried withmagnesium sulphate. After filtration and concentrating by evaporationunder a vacuum,2-amino-3-(2-bromo-4,5-difluorophenoxy)-2-methylpropionitrile isobtained as a crude product, which is further processed without furtherpurification.

c) A mixture of 300 mg of2-amino-3-(2-bromo-4,5-difluorophenoxy)-2-methylpropionitrile, 129 mg ofHunig's base, 270 mg of 4-trifluoromethoxy-benzoyl chloride and 12 mg of4-dimethylaminopyridine are stirred for 12 hours at room temperature in10 ml of dichloro-methane. Afterwards, the reaction mixture is dilutedby adding ethyl acetate, and is washed twice with each of a saturatedsodium bicarbonate solution, a 1N aqueous hydrochloric acid solution andfinally with brine, then the organic phase is concentrated byevaporation after filtration, and the residue is purified by flashchromatography, whereuponN-[2-cyano-1-(2-bromo-4,5-difluorophenoxy)-2-propyl]-4-trifluoromethoxy-benzamideis obtained.

d) 200 mg ofN-[2-cyano-1-(2-bromo-4,5-difluorophenoxy)-2-propyl]-4-trifluoromethoxy-benzamide,309 mg of 4-dimethylaminophenylboric acid and 6 ml of a saturated sodiumbicarbonate solution are mixed in 8 ml of toluene, rinsed with nitrogenfor 15 minutes and subsequently boiled under reflux for 2 days afteradding 66 mg of tetrakis(triphenyl-phosphine-palladium. Afterwards, theorganic phase is separated, the aqueous phase extracted three times withethyl acetate, the organic phases combined, dried with magnesiumsulphate, filtered and concentrated by evaporation under vacuum. Afterpurifying the residue by means of flash chromatography, the titlecompound is obtained with a melting point of 60-61° C.

The substances named in the following table may also be preparedanalogously to the above-described method. The values of the meltingpoints are given in ° C. TABLE 1

No. (R₈)_(m) R₉ (R₁₀)_(n) phys. data 1.1 4-F 2-(3-cyclopropylphenyl) 4-F1.2 4-F 2-(3-cyclopropylphenyl) 4-CF₃ 1.3 4-F 2-(3-cyclopropylphenyl)4-OCF₃ 1.4 4-F 2-(3-cyclopropylphenyl) 4-C(O)C₆H₅ 1.5 4-F2-(3-cyclopropylphenoxy) 4-F 1.6 4-F 2-(3-cyclopropylphenoxy) 4-CF₃ 1.74-F 2-(3-cyclopropylphenoxy) 4-OCF₃ 1.8 4-F 2-(3-cyclopropylphenoxy)4-C(O)C₆H₅ 1.9 4-F 2-(3-cyclopropoxyphenyl) 4-F 1.10 4-F2-(3-cyclopropoxyphenyl) 4-CF₃ 1.11 4-F 2-(3-cyclopropoxyphenyl) 4-OCF₃1.12 4-F 2-(3-cyclopropoxyphenyl) 4-C(O)C₆H₅ 1.13 4-F2-(3-cyclopropoxyphenoxy) 4-F 1.14 4-F 2-(3-cyclopropoxyphenoxy) 4-CF₃1.15 4-F 2-(3-cyclopropoxyphenoxy) 4-OCF₃ 1.16 4-F2-(3-cyclopropoxyphenoxy) 4-C(O)C₆H₅ 1.17 4-F 2-(4-cyclopropylphenyl)4-F 1.18 4-F 2-(4-cyclopropylphenyl) 4-CF₃ 1.19 4-F2-(4-cyclopropylphenyl) 4-OCF₃ 1.20 4-F 2-(4-cyclopropylphenyl)4-C(O)C₆H₅ 1.21 4-F 2-(4-cyclopropylphenoxy) 4-F 1.22 4-F2-(4-cyclopropylphenoxy) 4-CF₃ 1.23 4-F 2-(4-cyclopropylphenoxy) 4-OCF₃1.24 4-F 2-(4-cyclopropylphenoxy) 4-C(O)C₆H₅ 1.25 4-F2-(4-cyclopropoxyphenyl) 4-F 1.26 4-F 2-(4-cyclopropoxyphenyl) 4-CF₃1.27 4-F 2-(4-cyclopropoxyphenyl) 4-OCF₃ 1.28 4-F2-(4-cyclopropoxyphenyl) 4-C(O)C₆H₅ 1.29 4-F 2-(4-cyclopropoxyphenoxy)4-F 1.30 4-F 2-(4-cyclopropoxyphenoxy) 4-CF₃ 1.31 4-F2-(4-cyclopropoxyphenoxy) 4-OCF₃ 1.32 4-F 2-(4-cyclopropoxyphenoxy)4-C(O)C₆H₅ 1.33 4-F 2-(3-cyclobutylphenyl) 4-F 1.34 4-F2-(3-cyclobutylphenyl) 4-CF₃ 1.35 4-F 2-(3-cyclobutylphenyl) 4-OCF₃ 1.364-F 2-(3-cyclobutylphenyl) 4-C(O)C₆H₅ 1.37 4-F 2-(3-cyclobutylphenoxy)4-F 1.38 4-F 2-(3-cyclobutylphenoxy) 4-CF₃ 1.39 4-F2-(3-cyclobutylphenoxy) 4-OCF₃ 1.40 4-F 2-(3-cyclobutylphenoxy)4-C(O)C₆H₅ 1.41 4-F 2-(3-cyclobutoxyphenyl) 4-F 1.42 4-F2-(3-cyclobutoxyphenyl) 4-CF₃ 1.43 4-F 2-(3-cyclobutoxyphenyl) 4-OCF₃1.44 4-F 2-(3-cyclobutoxyphenyl) 4-C(O)C₆H₅ 1.45 4-F2-(3-cyclobutoxyphenoxy) 4-F 1.46 4-F 2-(3-cyclobutoxyphenoxy) 4-CF₃1.47 4-F 2-(3-cyclobutoxyphenoxy) 4-OCF₃ 1.48 4-F2-(3-cyctobutoxyphenoxy) 4-C(O)C₆H₅ 1.49 4-F 2-(4-cyclobutylphenyl) 4-F1.50 4-F 2-(4-cyclobutylphenyl) 4-CF₃ 1.51 4-F 2-(4-cyclobutylphenyl)4-OCF₃ 1.52 4-F 2-(4-cyclobutylphenyl) 4-C(O)C₆H₅ 1.53 4-F2-(4-cyclobutylphenoxy) 4-F 1.54 4-F 2-(4-cyclobutylphenoxy) 4-CF₃ 1.554-F 2-(4-cyclobutylphenoxy) 4-OCF₃ 1.56 4-F 2-(4-cyclobutylphenoxy)4-C(O)C₆H₅ 1.57 4-F 2-(4-cyclobutoxyphenyl) 4-F 1.58 4-F2-(4-cyclobutoxyphenyl) 4-CF₃ 1.59 4-F 2-(4-cyclobutoxyphenyl) 4-OCF₃1.60 4-F 2-(4-cyclobutoxyphenyl) 4-C(O)C₆H₅ 1.61 4-F2-(4-cyclobutoxyphenoxy) 4-F 1.62 4-F 2-(4-cyclobutoxyphenoxy) 4-CF₃1.63 4-F 2-(4-cyclobutoxyphenoxy) 4-OCF₃ 1.64 4-F2-(4-cyclobutoxyphenoxy) 4-C(O)C₆H₅ 1.65 4-F 2-(4-N(CH₃)₂-phenyl) 4-F1.66 4-F 2-(4-N(CH₃)₂-phenyl) 4-CF₃ 1.67 4-F 2-(4-N(CH₃)₂-phenyl) 4-OCF₃1.68 4-F 2-(4-N(CH₃)₂-phenyl) 4-C(O)C₆H₅ 1.69 4-F 2-(4-N(CH₃)₂-phenoxy)4-F 1.70 4-F 2-(4-N(CH₃)₂-phenoxy) 4-CF₃ 1.71 4-F 2-(4-N(CH₃)₂-phenoxy)4-OCF₃ 1.72 4-F 2-(4-N(CH₃)₂-phenoxy) 4-C(O)C₆H₅ 1.73 4-F2-(3-N(CH₃)₂-phenoxy) 4-F 1.74 4-F 2-(3-N(CH₃)₂-phenoxy) 4-CF₃ 1.75 4-F2-(3-N(CH₃)₂-phenoxy) 4-OCF₃ 1.76 4-F 2-(3-N(CH₃)₂-phenoxy) 4-C(O)C₆H₅1.77 4-F 2-(2-N(CH₃)₂-phenoxy) 4-F 1.78 4-F 2-(2-N(CH₃)₂-phenoxy) 4-CF₃1.79 4-F 2-(2-N(CH₃)₂-phenoxy) 4-OCF₃ 1.80 4-F 2-(2-N(CH₃)₂-phenoxy)4-C(O)C₆H₅ 1.81 4-F 2-((3,4-OCH₂O)phenyl 4-F 1.82 4-F2-((3,4-OCH₂O)phenyl 4-CF₃ 1.83 4-F 2-((3,4-OCH₂O)phenyl 4-OCF₃ 1.84 4-F2-((3,4-OCH₂O)phenyl 4-C(O)C₆H₅ 1.85 5-Cl 2-(3-cyclopropylphenyl) 4-F1.86 5-Cl 2-(3-cyclopropylphenyl) 4-CF₃ 1.87 5-Cl2-(3-cyclopropylphenyl) 4-OCF₃ 1.88 5-Cl 2-(3-cyclopropylphenyl)4-C(O)C₆H₅ 1.89 5-Cl 2-(3-cyclopropylphenoxy) 4-F 1.90 5-Cl2-(3-cyclopropylphenoxy) 4-CF₃ 1.91 5-Cl 2-(3-cyclopropylphenoxy) 4-OCF₃1.92 5-Cl 2-(3-cyclopropylphenoxy) 4-C(O)C₆H₅ 1.93 5-Cl2-(3-cyclopropoxyphenyl) 4-F 1.94 5-Cl 2-(3-cyclopropoxyphenyl) 4-CF₃1.95 5-Cl 2-(3-cyclopropoxyphenyl) 4-OCF₃ 1.96 5-Cl2-(3-cyclopropoxyphenyl) 4-C(O)C₆H₅ 1.97 5-Cl 2-(3-cyclopropoxyphenoxy)4-F 1.98 5-Cl 2-(3-cyclopropoxyphenoxy) 4-CF₃ 1.99 5-Cl2-(3-cyclopropoxyphenoxy) 4-OCF₃ 1.100 5-Cl 2-(3-cyclopropoxyphenoxy)4-C(O)C₆H₅ 1.101 5-Cl 2-(4-cyclopropylphenyl) 4-F 1.102 5-Cl2-(4-cyclopropylphenyl) 4-CF₃ 1.103 5-Cl 2-(4-cyclopropylphenyl) 4-OCF₃1.104 5-Cl 2-(4-cyclopropylphenyl) 4-C(O)C₆H₅ 1.105 5-Cl2-(4-cyclopropylphenoxy) 4-F 1.106 5-Cl 2-(4-cyclopropylphenoxy) 4-CF₃1.107 5-Cl 2-(4-cyclopropylphenoxy) 4-OCF₃ 1.108 5-Cl2-(4-cyclopropylphenoxy) 4-C(O)C₆H₅ 1.109 5-Cl 2-(4-cyclopropoxyphenyl)4-F 1.110 5-Cl 2-(4-cyclopropoxyphenyl) 4-CF₃ 1.111 5-Cl2-(4-cyclopropoxyphenyl) 4-OCF₃ 1.112 5-Cl 2-(4-cyclopropoxyphenyl)4-C(O)C₆H₅ 1.113 5-Cl 2-(4-cyclopropoxyphenoxy) 4-F 1.114 5-Cl2-(4-cyclopropoxyphenoxy) 4-CF₃ 1.115 5-Cl 2-(4-cyclopropoxyphenoxy)4-OCF₃ 1.116 5-Cl 2-(4-cyclopropoxyphenoxy) 4-C(O)C₆H₅ 1.117 5-Cl2-(3-cyclobutylphenyl) 4-F 1.118 5-Cl 2-(3-cyclobutylphenyl) 4-CF₃ 1.1195-Cl 2-(3-cyclobutylphenyl) 4-OCF₃ 1.120 5-Cl 2-(3-cyclobutylphenyl)4-C(O)C₆H₅ 1.121 5-Cl 2-(3-cyclobutylphenoxy) 4-F 1.122 5-Cl2-(3-cyclobutylphenoxy) 4-CF₃ 1.123 5-Cl 2-(3-cyclobutylphenoxy) 4-OCF₃1.124 5-Cl 2-(3-cyclobutylphenoxy) 4-C(O)C₆H₅ 1.125 5-Cl2-(3-cyclobutoxyphenyl) 4-F 1.126 5-Cl 2-(3-cyclobutoxyphenyl) 4-CF₃1.127 5-Cl 2-(3-cyclobutoxyphenyl) 4-OCF₃ 1.128 5-Cl2-(3-cyclobutoxyphenyl) 4-C(O)C₆H₅ 1.129 5-Cl 2-(3-cyclobutoxyphenoxy)4-F 1.130 5-Cl 2-(3-cyclobutoxyphenoxy) 4-CF₃ 1.131 5-Cl2-(3-cyclobutoxyphenoxy) 4-OCF₃ 1.132 5-Cl 2-(3-cyclobutoxyphenoxy)4-C(O)C₆H₅ 1.133 5-Cl 2-(4-cyclobutylphenyl) 4-F 1.134 5-Cl2-(4-cyclobutylphenyl) 4-CF₃ 1.135 5-Cl 2-(4-cyclobutylphenyl) 4-OCF₃1.136 5-Cl 2-(4-cyclobutylphenyl) 4-C(O)C₆H₅ 1.137 5-Cl2-(4-cyclobutylphenoxy) 4-F 1.138 5-Cl 2-(4-cyclobutylphenoxy) 4-CF₃1.139 5-Cl 2-(4-cyclobutylphenoxy) 4-OCF₃ 1.140 5-Cl2-(4-cyclobutylphenoxy) 4-C(O)C₆H₅ 1.141 5-Cl 2-(4-cyclobutoxyphenyl)4-F 1.142 5-Cl 2-(4-cyclobutoxyphenyl) 4-CF₃ 1.143 5-Cl2-(4-cyclobutoxyphenyl) 4-OCF₃ 1.144 5-Cl 2-(4-cyclobutoxyphenyl)4-C(O)C₆H₅ 1.145 5-Cl 2-(4-cyclobutoxyphenoxy) 4-F 1.146 5-Cl2-(4-cyclobutoxyphenoxy) 4-CF₃ 1.147 5-Cl 2-(4-cyclobutoxyphenoxy)4-OCF₃ 1.148 5-Cl 2-(4-cyclobutoxyphenoxy) 4-C(O)C₆H₅ 1.149 5-Cl2-(4-N(CH₃)₂-phenyl) 4-F 1.150 5-Cl 2-(4-N(CH₃)₂-phenyl) 4-CF₃ 1.1515-Cl 2-(4-N(CH₃)₂-phenyl) 4-OCF₃ 1.152 5-Cl 2-(4-N(CH₃)₂-phenyl)4-C(O)C₆H₅ 1.153 5-Cl 2-(4-N(CH₃)₂-phenoxy) 4-F 1.154 5-Cl2-(4-N(CH₃)₂-phenoxy) 4-CF₃ 1.155 5-Cl 2-(4-N(CH₃)₂-phenoxy) 4-OCF₃1.156 5-Cl 2-(4-N(CH₃)₂-phenoxy) 4-C(O)C₆H₅ 1.157 5-Cl2-(3-N(CH₃)₂-phenoxy) 4-F 1.158 5-Cl 2-(3-N(CH₃)₂-phenoxy) 4-CF₃ 1.1595-Cl 2-(3-N(CH₃)₂-phenoxy) 4-OCF₃ 1.160 5-Cl 2-(3-N(CH₃)₂-phenoxy)4-C(O)C₆H₅ 1.161 5-Cl 2-(2-N(CH₃)₂-phenoxy) 4-F 1.162 5-Cl2-(2-N(CH₃)₂-phenoxy) 4-CF₃ 1.163 5-Cl 2-(2-N(CH₃)₂-phenoxy) 4-OCF₃1.164 5-Cl 2-(2-N(CH₃)₂-phenoxy) 4-C(O)C₆H₅ 1.165 5-Cl2-((3,4-OCH₂O)phenyl 4-F 1.166 5-Cl 2-((3,4-OCH₂O)phenyl 4-CF₃ 1.1675-Cl 2-((3,4-OCH₂O)phenyl 4-OCF₃ 1.168 5-Cl 2-((3,4-OCH₂O)phenyl4-C(O)C₆H₅ 1.169 4,5-F₂ 2-(3-cyclopropylphenyl) 4-F 1.170 4,5-F₂2-(3-cyclopropylphenyl) 4-CF₃ 1.171 4,5-F₂ 2-(3-cyclopropylphenyl)4-OCF₃ 1.172 4,5-F₂ 2-(3-cyclopropylphenyl) 4-C(O)C₆H₅ 1.173 4,5-F₂2-(3-cyclopropylphenoxy) 4-F 1.174 4,5-F₂ 2-(3-cyclopropylphenoxy) 4-CF₃1.175 4,5-F₂ 2-(3-cyclopropylphenoxy) 4-OCF₃ 1.176 4,5-F₂2-(3-cyclopropylphenoxy) 4-C(O)C₆H₅ 1.177 4,5-F₂2-(3-cyclopropoxyphenyl) 4-F 1.178 4,5-F₂ 2-(3-cyclopropoxyphenyl) 4-CF₃1.179 4,5-F₂ 2-(3-cyclopropoxyphenyl) 4-OCF₃ 1.180 4,5-F₂2-(3-cyclopropoxyphenyl) 4-C(O)C₆H₅ 1.181 4,5-F₂2-(3-cyclopropoxyphenoxy) 4-F 1.182 4,5-F₂ 2-(3-cyclopropoxyphenoxy)4-CF₃ 1.183 4,5-F₂ 2-(3-cyclopropoxyphenoxy) 4-OCF₃ 1.184 4,5-F₂2-(3-cyclopropoxyphenoxy) 4-C(O)C₆H₅ 1.185 4,5-F₂2-(4-cyclopropylphenyl) 4-F 1.186 4,5-F₂ 2-(4-cyclopropylphenyl) 4-CF₃1.187 4,5-F₂ 2-(4-cyclopropylphenyl) 4-OCF₃ 1.188 4,5-F₂2-(4-cyclopropylphenyl) 4-C(O)C₆H₅ 1.189 4,5-F₂ 2-(4-cyclopropylphenoxy)4-F 1.190 4,5-F₂ 2-(4-cyclopropylphenoxy) 4-CF₃ 1.191 4,5-F₂2-(4-cyclopropylphenoxy) 4-OCF₃ 1.192 4,5-F₂ 2-(4-cyclopropylphenoxy)4-C(O)C₆H₅ 1.193 4,5-F₂ 2-(4-cyclopropoxyphenyl) 4-F 1.194 4,5-F₂2-(4-cyclopropoxyphenyl) 4-CF₃ 1.195 4,5-F₂ 2-(4-cyclopropoxyphenyl)4-OCF₃ 1.196 4,5-F₂ 2-(4-cyclopropoxyphenyl) 4-C(O)C₆H₅ 1.197 4,5-F₂2-(4-cyclopropoxyphenoxy) 4-F 1.198 4,5-F₂ 2-(4-cyclopropoxyphenoxy)4-CF₃ 1.199 4,5-F₂ 2-(4-cyclopropoxyphenoxy) 4-OCF₃ 1.200 4,5-F₂2-(4-cyclopropoxyphenoxy) 4-C(O)C₆H₅ 1.201 4,5-F₂ 2-(3-cyclobutylphenyl)4-F 1.202 4,5-F₂ 2-(3-cyclobutylphenyl) 4-CF₃ 1.203 4,5-F₂2-(3-cyclobutylphenyl) 4-OCF₃ 1.204 4,5-F₂ 2-(3-cyclobutylphenyl)4-C(O)C₆H₅ 1.205 4,5-F₂ 2-(3-cyclobutylphenoxy) 4-F 1.206 4,5-F₂2-(3-cyclobutylphenoxy) 4-CF₃ 1.207 4,5-F₂ 2-(3-cyclobutylphenoxy)4-OCF₃ 1.208 4,5-F₂ 2-(3-cyclobutylphenoxy) 4-C(O)C₆H₅ 1.209 4,5-F₂2-(3-cyclobutoxyphenyl) 4-F 1.210 4,5-F₂ 2-(3-cyclobutoxyphenyl) 4-CF₃1.211 4,5-F₂ 2-(3-cyclobutoxyphenyl) 4-OCF₃ 1.212 4,5-F₂2-(3-cyclobutoxyphenyl) 4-C(O)C₆H₅ 1.213 4,5-F₂ 2-(3-cyclobutoxyphenoxy)4-F 1.214 4,5-F₂ 2-(3-cyclobutoxyphenoxy) 4-CF₃ 1.215 4,5-F₂2-(3-cyclobutoxyphenoxy) 4-OCF₃ 1.216 4,5-F₂ 2-(3-cyclobutoxyphenoxy)4-C(O)C₆H₅ 1.217 4,5-F₂ 2-(4-cyclobutylphenyl) 4-F 1.218 4,5-F₂2-(4-cyclobutylphenyl) 4-CF₃ 1.219 4,5-F₂ 2-(4-cyclobutylphenyl) 4-OCF₃1.220 4,5-F₂ 2-(4-cyclobutylphenyl) 4-C(O)C₆H₅ 1.221 4,5-F₂2-(4-cyclobutylphenoxy) 4-F 1.222 4,5-F₂ 2-(4-cyclobutylphenoxy) 4-CF₃1.223 4,5-F₂ 2-(4-cyclobutylphenoxy) 4-OCF₃ 1.224 4,5-F₂2-(4-cyclobutylphenoxy) 4-C(O)C₆H₅ 1.225 4,5-F₂ 2-(4-cyclobutoxyphenyl)4-F 1.226 4,5-F₂ 2-(4-cyclobutoxyphenyl) 4-CF₃ 1.227 4,5-F₂2-(4-cyclobutoxyphenyl) 4-OCF₃ 1.228 4,5-F₂ 2-(4-cyclobutoxyphenyl)4-C(O)C₆H₅ 1.229 4,5-F₂ 2-(4-cyclobutoxyphenoxy) 4-F 1.230 4,5-F₂2-(4-cyclobutoxyphenoxy) 4-CF₃ 1.231 4,5-F₂ 2-(4-cyclobutoxyphenoxy)4-OCF₃ 1.232 4,5-F₂ 2-(4-cyclobutoxyphenoxy) 4-C(O)C₆H₅ 1.233 4,5-F₂2-(4-N(CH₃)₂-phenyl) 4-F 1.234 4,5-F₂ 2-(4-N(CH₃)₂-phenyl) 4-CF₃ 1.2354,5-F₂ 2-(4-N(CH₃)₂-phenyl) 4-OCF₃ m.p. 60-1° 1.236 4,5-F₂2-(4-N(CH₃)₂-phenyl) 4-C(O)C₆H₅ 1.237 4,5-F₂ 2-(4-N(CH₃)₂-phenoxy) 4-F1.238 4,5-F₂ 2-(4-N(CH₃)₂-phenoxy) 4-CF₃ 1.239 4,5-F₂2-(4-N(CH₃)₂-phenoxy) 4-OCF₃ 1.240 4,5-F₂ 2-(4-N(CH₃)₂-phenoxy)4-C(O)C₆H₅ 1.241 4,5-F₂ 2-(3-N(CH₃)₂-phenoxy) 4-F 1.242 4,5-F₂2-(3-N(CH₃)₂-phenoxy) 4-CF₃ 1.243 4,5-F₂ 2-(3-N(CH₃)₂-phenoxy) 4-OCF₃1.244 4,5-F₂ 2-(3-N(CH₃)₂-phenoxy) 4-C(O)C₆H₅ 1.245 4,5-F₂2-(2-N(CH₃)₂-phenoxy) 4-F 1.246 4,5-F₂ 2-(2-N(CH₃)₂-phenoxy) 4-CF₃ 1.2474,5-F₂ 2-(2-N(CH₃)₂-phenoxy) 4-OCF₃ 1.248 4,5-F₂ 2-(2-N(CH₃)₂-phenoxy)4-C(O)C₆H₅ 1.249 4,5-F₂ 2-((3,4-OCH₂O)phenyl 4-F 1.250 4,5-F₂2-((3,4-OCH₂O)phenyl 4-CF₃ 1.251 4,5-F₂ 2-((3,4-OCH₂O)phenyl 4-OCF₃ m.p.172-3° 1.252 4,5-F₂ 2-((3,4-OCH₂O)phenyl 4-C(O)C₆H₅

BIOLOGICAL EXAMPLES 1. In-Vivo Test on Trichostrongylus colubriformisand Haemonchus contortus on Mongolian Gerbils (Meriones unguiculatus)Using Peroral Application

Six to eight week old Mongolian gerbils are infected by artificialfeeding with ca. 2000 third instar larvae each of T. colubriformis andH. contortus. 6 days after infection, the gerbils are lightlyanaesthetised with N₂O and treated by peroral application with the testcompounds, dissolved in a mixture of 2 parts DMSO and 1 partpolyethylene glycol (PEG 300), in quantities of 100, 32 and 10-0.1mg/kg. On day 9 (3 days after treatment), when most of the H. contortusthat are still present are late 4th instar larvae and most of the T.colubriformis are immature adults, the gerbils are killed in order tocount the worms. The efficacy is calculated as the % reduction of thenumber of worms in each gerbil, compared with the geometric average ofnumber of worms from 8 infected and untreated gerbils.

In this test, a vast reduction in nematode infestation is achieved withcompounds of formula I.

To examine the insecticidal and/or acarcidal activity of the compoundsof formula I on animals and plants, the following test methods may beused.

2. Activity on L₁ Larvae of Lucilla selicata

1 ml of an aqueous suspension of the active substance to be tested isadmixed with 3 ml of a special larvae growth medium at ca. 50° C., sothat a homogenate of either 250 or 125 ppm of active ingredient contentis obtained. Ca. 30 Lucilla larvae (L₁) are used in each test tubesample. After 4 days, the mortality rate is determined.

3. Acaricidal Activity on Boophilus microplus (Blarra Strain)

A piece of sticky tape is attached horizontally to a PVC sheet, so that10 fully engorged female ticks of Boophilus microplus (Biarra strain)can be adhered thereto by their backs, side by side, in a row. Using aninjection needle, 1 μl of a liquid is injected into each tick. Theliquid is a 1:1 mixture of polyethylene glycol and acetone and itcontains, dissolved therein, a certain amount of active ingredientchosen from 1, 0.1 or 0.01 μg per tick. Control animals are given aninjection without active ingredient. After treatment, the animals arekept under normal conditions in an insectarium at ca. 28° C. and at 80%relative humidity until oviposition takes place and the larvae havehatched from the eggs of the control animals. The activity of a testedsubstance is determined by IR₉₀, i.e. an evaluation is made of thedosage of active ingredient at which 9 out of 10 female ticks (=90%) layeggs that are infertile even after 30 days.

4. In Vitro Efficacy on Engorged Female Boophilus microplus (BIARRA)

4×10 engorged female ticks of the OP-resistant BIARRA strain are adheredto a sticky strip and covered for 1 hour with a cotton-wool ball soakedin an emulsion or suspension of the test compound in concentrations of500, 125, 31 and 8 ppm respectively. Evaluation takes place 28 dayslater based on mortality, oviposition and hatched larvae.

An indication of the activity of the test compounds is shown by thenumber of females that

-   -   die quickly before laying eggs,    -   survive for some time without laying eggs,    -   lay eggs in which no embryos are formed,    -   lay eggs in which embryos form, from which no larvae hatch, and    -   lay eggs in which embryos form, from which larvae normally hatch        within 26 to 27 days.

5. In Vitro Efficacy on Nymphs of Amblyomma hebraeum

About 5 fasting nymphs are placed in a polystyrene test tube containing2 ml of the test compound in solution, suspension or emulsion.

After immersion for 10 minutes, and shaking for 2×10 seconds on a vortexmixer, the test tubes are blocked up with a tight wad of cotton wool androtated. As soon as all the liquid has been soaked up by the cotton woolball, it is pushed half-way into the test tube which is still beingrotated, so that most of the liquid is squeezed out of the cotton-woolball and flows into a Petri dish below.

The test tubes are then kept at room temperature in a room with daylightuntil evaluated. After 14 days, the test tubes are immersed in a beakerof boiling water. If the ticks begin to move in reaction to the heat,the test substance is inactive at the tested concentration, otherwisethe ticks are regarded as dead and the test substances regarded asactive at the tested concentration. All substances are tested in aconcentration range of 0.1 to 100 ppm.

6. Activity Against Dermanyssus gallinae

2 to 3 ml of a solution containing 10 ppm active ingredient, and ca. 200mites (Dermanyssus gallinae) at different stages of development areadded to a glass container which is open at the top. Then the containeris dosed with a wad of cotton wool, shaken for 10 minutes until themites are completely wet, and then inverted briefly so that theremaining test solution can be absorbed by the cotton wool. After 3days, the mortality of the mites is determined by counting the deadindividuals and indicated as a percentage.

7. Activity Against Musca domestica

A sugar cube is treated with a solution of the test substance in such away that the concentration of test substance in the sugar, after dryingover night, is 250 ppm. The cube treated in this way is placed on analuminum dish with wet cotton wool and 10 adult Musca domestica of anOP-resistant strain, covered with a beaker and incubated at 25° C. Themortality rate is determined after 24 hours.

1. A compound of formula I in free form or in salt form

wherein A₁ and A₂, independently of one another, signify unsubstitutedaryl or aryl which is substituted once or many times, whereby thesubstituents of A₁ and A₂, independently of one another, are selectedfrom the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl,halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyl,halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy,halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio,C₁-C₆-alkylsulfonyloxy, halo-C₁-C₆-alkylsulfonyloxy,C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio,C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl,C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino,di-C₁-C₆-alkylamino, C₁-C₆-alkylsulfonylamino,halo-C₁-C₆-alkylsulfonylamino, C₁-C₆-alkylcarbonyl,halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, unsubstitutedphenylamino or phenylamino which is substituted once or many times,unsubstituted phenylcarbonyl or phenylcarbonyl which is substituted onceor many times, unsubstituted phenylmethoximino or phenylmethoximinowhich is substituted once or many times, unsubstitutedphenylhydroxymethyl or phenylhydroxymethyl which is substituted once ormany times, unsubstituted 1-phenyl-1-hydroxyethyl or1-phenyl-1-hydroxyethyl which is substituted once or many times,unsubstituted phenylchloromethyl or phenylchloromethyl which issubstituted once or many times, unsubstituted phenylcyanomethyl orphenylcyanomethyl which is substituted once or many times; unsubstitutedphenyl or phenyl which is substituted once or many times; unsubstitutedphenoxy or phenoxy which is substituted once or many times;unsubstituted phenyacetylenyl or phenyacetylenyl which is substitutedonce or many times, and unsubstituted pyridyloxy or pyridyloxy which issubstituted once or many times, whereby the substituents may each beindependent of one another and are selected from R₉; or unsubstitutedhetaryl or hetaryl which is substituted once or many times and is boundby a ring carbon atom, whereby the substituents of A₁ and A₂ may beindependent of one another and are selected from R₉; R₁ signifieshydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, allyl or C₁-C₆-alkoxymethyl;R₂, R₃, R₄, R₅ and R₆ are either, independently of one another,hydrogen, halogen, unsubstituted C₁-C₆-alkyl or C₁-C₆-alkyl which issubstituted once or many times, unsubstituted C₂-C₆-alkenyl orC₂-C₆-alkenyl which is substituted once or many times, unsubstitutedC₂-C₆-alkinyl or C₂-C₆-alkinyl which is substituted once or many times,unsubstituted C₁-C₆-alkoxy or C₁-C₆-alkoxy which is substituted once ormany times, whereby the substituents may each be independent of oneanother and are selected from the group consisting of halogen,C₁-C₆-alkoxy und halo-C₁-C₆-alkoxy; unsubstituted C₃-C₆-cycloalkyl orC₃-C₆-cycloalkyl which is substituted once or many times, whereby thesubstituents may be independent of one another and are selected from thegroup consisting of halogen and C₁-C₆-alkyl; or unsubstituted phenyl orphenyl which is substituted once or many times, whereby the substituentsmay be independent of one another and are selected from the groupconsisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio,C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino or di-C₁-C₆-alkylamino; or R₂and R₃ together signify C₂-C₆-alkylene; R₇ signifies hydrogen orC₁-C₆-alkyl; either R₈ signifies C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₃-C₈-cycloalkyl, halo-C₃-C₈-cycloalkyl, C₃-C₈-cycloalkylamino,halo-C₃-C₈-cycloalkylamino, C₃-C₈-cycloalkoxy, halo-C₃-C₈-cycloalkoxy orC₃-C₈-cycloalkylthio; and R_(8′) signifies hydrogen or R₉; or R₈ andR_(8′) together signify unsubstituted or R₉-substituted C₃C₅-alkylene,whereby one or two carbon atoms may be replaced by O, N or S; R₉signifies halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl,C₂-C₆-alkinyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy,C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkylthio, C₂-C₆-alkenyloxy,halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio,C₁-C₆-alkylsulfonyloxy, halo-C₁-C₆-alkylsulfonyloxy,C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio,C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl,C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino,di-C₁-C₆-alkylamino, C₁-C₆-alkylsulfonylamino,halo-C₁-C₆-alkylsulfonylamino, C₁-C₆-alkylcarbonyl,halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonylor di-C₁-C₆-alkylaminocarbonyl; W signifies O, S, S(O₂) or N(R₇); Xsignifies O or N(R₇); a signifies 1, 2, 3 or 4; b signifies 0, 1, 2, 3or 4; and c is 0 or
 1. 2. Compounds of formula I, respectively in freeform or in salt form, according to claim 1, wherein A₁ and A₂,independently of one another, signify aryl which is unsubstituted orsubstituted once or many times, whereby the substituents of A₁ and A₂,independently of one another, are selected from the group consisting ofhalogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy,halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy,halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio,C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino,di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl, unsubstituted phenylamino or phenylaminosubstituted once or many times; phenylcarbonyl which is unsubstituted orsubstituted once or many times; phenyl which is unsubstituted orsubstituted once or many times; phenoxy which is unsubstituted orsubstituted once or many times; and pyridyloxy which is unsubstituted orsubstituted once or many times, whereby the substituents may each beindependent of one another and are selected from the group consisting ofhalogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy,halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy,C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkylthio, C₁-C₆-alkylthio,halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl,C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl,halo-C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl; or unsubstitutedhetaryl or hetaryl which is substituted once or many times and is boundby a ring carbon atom, whereby the substituents of A₁ and A₂ may beindependent of one another and are selected from the group consisting ofhalogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy,halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy,C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkylthio, C₁-C₆-alkylthio,halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl,C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl,halo-C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl;
 3. Compounds offormula I, respectively in free form or in salt form, according to claim1, wherein A₁ and A₂, independently of one another, signify aryl whichis unsubstituted or is substituted once or many times, whereby thesubstituents of A₁ and A₂, independently of one another, are selectedfrom the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl,halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₃-C₅-cycloalkyl,C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl,halo-C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, unsubstituted phenyl orphenyl which is substituted once or many times; phenoxy which isunsubstituted or substituted once or many times; and pyridyloxy which isunsubstituted or substituted once or many times, whereby thesubstituents are each independent of one another and are selected fromthe group consisting of halogen, nitro, cyano, C₁-C₄-alkyl,halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₃-C₅-cycloalkyl,C₃-C₅-cycloalkyloxy, C₃-C5-cycloalkylamino, C₃-C₅-cycloalkylthio,C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio, C₁-C₄-alkylamino,di-C₁-C₄-alkylamino, C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl andC₁-C₄-alkoxycarbonyl; or unsubstituted hetaryl or hetaryl which issubstituted once or many times and is bound by a ring carbon atom,whereby the substituents of A₁ and A₂ may be independent of one anotherand are selected from the group consisting of halogen, nitro, cyano,C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,C₃-C₅-cycloalkyl, C₃-C₅-cycloalkyloxy, C₃-C₅-cycloalkylamino,C₃-C₅-cycloalkylthio, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkylcarbonyl,halo-C₁-C₄-alkylcarbonyl and C₁-C₄-alkoxycarbonyl;
 4. Compounds offormula I, respectively in free form or in salt form, according to claim1, wherein A₁ and A₂, independently of one another, signify aryl whichis unsubstituted or is substituted once or many times, whereby thesubstituents of A₁ and A₂, independently of one another, are selectedfrom the group consisting of halogen, nitro, cyano, C₁-C₂-alkyl,halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₃-C₅-cycloalkyl,C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio, C₁-C₂-alkylcarbonyl,halo-C₁-C₂-alkylcarbonyl, C₁-C₂-alkoxycarbonyl, and unsubstituted phenylor phenyl which is substituted once or many times, whereby thesubstituents are each independent of one another and are selected fromthe group consisting of halogen, nitro, cyano, C₁-C₂-alkyl,halo-C₁-C₂-alkyl, C₁-C₂-alkoxy, halo-C₁-C₂-alkoxy, C₃-C₄-cycloalkyl,C₃-C₄-cycloalkyloxy, C₃-C₄-cycloalkylamino, C₃-C₄-cycloalkylthio,C₁-C₂-alkylthio, halo-C₁-C₂-alkylthio, C₁-C₂-alkylamino,di-C₁-C₂-alkylamino, C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl andC₁-C₂-alkoxycarbonyl;
 5. Compounds of formula I, respectively in freeform or in salt form, according to claim 1, wherein R₁ is hydrogen,C₁-C₄-alkyl, halo-C₁-C₄-alkyl or C₁-C₄-alkoxymethyl.
 6. Compounds offormula I, respectively in free form or in salt form, according to claim1, wherein R₁ is hydrogen, C₁-C₂-alkyl or halo-C₁-C₂-alkyl.
 7. Compoundsof formula I, respectively in free form or in salt form, according toclaim 1, wherein R₁ is hydrogen or C₁-C₂-alkyl.
 8. Compounds of formulaI, respectively in free form or in salt form, according to claim 1,wherein R₂, R₃, R₄, R₅ and R₆, independently of one another, signifyhydrogen, halogen, unsubstituted C₁-C₄-alkyl or C₁-C₄-alkyl which issubstituted once or many times, whereby the substituents may beindependent of one another and are selected from the group consisting ofhalogen and C₁-C₄-alkoxy; C₃-C₅-cycloalkyl or phenyl which isunsubstituted or is substituted once or many times, whereby thesubstituents may be independent of one another and are selected from thegroup consisting of halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxyand halo-C₁-C₄-alkoxy.
 9. Compounds of formula I, respectively in freeform or in salt form, according to claim 1, wherein R₂, R₃, R₄, R₅ andR₆, independently of one another, signify hydrogen, unsubstitutedC₁-C₄-alkyl or C₁-C₄-alkyl which is substituted once or many times,whereby the substituents may be independent of one another and areselected from the group consisting of halogen and C₁-C₂-alkoxy; orC₃-C₅-cycloalkyl.
 10. Compounds of formula I, respectively in free formor in salt form, according to claim 1, wherein R₂, R₃, R₄, R₅ and R₆independently of one another are hydrogen, C₁-C₂-alkyl or—C₃-C₅-cycloalkyl.
 11. Compounds of formula I, respectively in free formor in salt form, according to claim 1, wherein R₇ is C₁-C₆-alkyl. 12.Compounds of formula I, respectively in free form or in salt form,according to claim 1, wherein R₇ is C₁-C₄-alkyl.
 13. Compounds offormula I, respectively in free form or in salt form, according to claim1, wherein R₇ is C₁-C₂-alkyl.
 14. Compounds of formula I, respectivelyin free form or in salt form, according to claim 1, wherein either R₈ isC₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₃-C₆-cycloalkyl orC₃-C₆-cycloalkoxy; and R₈ is hydrogen, or R₈ and R_(8′) together signifyunsubstituted or R₉-substituted C₃-C₄-alkylene, whereby one or twocarbon atoms may be replaced by O or N.
 15. Compounds of formula I,respectively in free form or in salt form, according to claim 1, whereineither R₈ is C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, and R_(8′) ishydrogen, or R₈ and R_(8′) together are unsubstituted or R₉-substitutedC₃-alkylene, whereby one or two carbon atoms may be replaced by O. 16.Compounds of formula I, respectively in free form or in salt form,according to claim 1, wherein R₈ is C₁-C₄-alkylamino ordi-C₁-C₄-alkylamino, and R_(8′) is hydrogen.
 17. Compounds of formula I,respectively in free form or in salt form, according to claim 1, whereinR₉ signifies halogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₂-C₅-alkenyl, halo-C₂-C₅-alkenyl,C₂-C₅-alkinyl, C₃-C₅-cycloalkyl, C₃-C₅-cycloalkyloxy,C₃-C₅-cycloalkylamino, C₃-C₅-cycloalkylthio, C₂-C₅-alkenyloxy,halo-C₂-C₅-alkenyloxy, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,C₁-C₄-alkylsulfonyloxy, halo-C₁-C₄-alkylsulfonyloxy,C₁-C₄-alkylsulfonyl, halo-C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino,di-C₁-C₄-alkylamino, C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl ordi-C₁-C₄-alkylaminocarbonyl.
 18. Compounds of formula I, respectively infree form or in salt form, according to claim 1, wherein R₉ signifieshalogen, cyano, C₁-C₃-alkyl, halo-C₁-C₃-alkyl, C₁-C₃-alkoxy,halo-C₁-C₃-alkoxy, C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyloxy,C₃-C₄-cycloalkylamino, C₁-C₃-alkylthio, halo-C₁-C₃-alkylthio,C₁-C₃-alkylsulfonyl, halo-C₁-C₃-alkylsulfonyl, C₁-C₃-alkylamino,di-C₁-C₃-alkylamino, C₁-C₃-alkylcarbonyl, halo-C₁-C₃-alkylcarbonyl orC₁-C₃-alkoxycarbonyl.
 19. Compounds of formula I, respectively in freeform or in salt form, according to claim 1, wherein R₉ signifieshalogen, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy,halo-C₁-C₂-alkoxy, C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyloxy,C₁-C₂-alkylthio or halo-C₁-C₂-alkylthio.
 20. Compounds of formula I,respectively in free form or in salt form, according to claim 1, whereinW is O or S.
 21. Compounds of formula I, respectively in free form or insalt form, according to claim 1, wherein W is O.
 22. Compounds offormula I, respectively in free form or in salt form, according to claim1, wherein X is O or N(R₇).
 23. Compounds of formula I, respectively infree form or in salt form, according to claim 1, wherein X is O. 24.Compounds of formula I, respectively in free form or in salt form,according to claim 1, wherein a is 1, 2 or
 3. 25. Compounds of formulaI, respectively in free form or in salt form, according to claim 1,wherein a is 1 or
 2. 26. Compounds of formula I, respectively in freeform or in salt form, according to claim 1, wherein a is
 1. 27.Compounds of formula I, respectively in free form or in salt form,according to claim 1, wherein b is 0, 1 or
 2. 28. Compounds of formulaI, respectively in free form or in salt form, according to claim 1,wherein b is 0 or
 1. 29. Compounds of formula I, respectively in freeform or in salt form, according to claim 1, wherein b is
 0. 30.Compounds of formula I, respectively in free form or in salt form,according to claim 1, wherein c is
 0. 31. Compounds of formula I,respectively in free form or in salt form, according to claim 1, whereinA₁ and A₂, independently of one another, signify aryl which isunsubstituted or substituted once or many times, whereby thesubstituents of A₁ and A₂, independently of one another, are selectedfrom the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl,halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio,halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl,C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl,halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, unsubstitutedphenylamino or phenylamino substituted once or many times;phenylcarbonyl which is unsubstituted or substituted once or many times;phenyl which is unsubstituted or substituted once or many times; phenoxywhich is unsubstituted or substituted once or many times; and pyridyloxywhich is unsubstituted or substituted once or many times, whereby thesubstituents may each be independent of one another and are selectedfrom the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl,halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkylthio,C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl,halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl;or unsubstituted hetaryl or hetaryl which is substituted once or manytimes and is bound by a ring carbon atom, whereby the substituents of A₁and A₂ may be independent of one another and are selected from the groupconsisting of halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy,C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkylthio, C₁-C₆-alkylthio,halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl,C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl,halo-C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl; R₁ signifieshydrogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl or C₁-C₄-alkoxymethyl; R₂, R₃,R₄, R₅ and R₆, independently of one another, signify hydrogen, halogen,unsubstituted C₁-C₄-alkyl or C₁-C₄-alkyl which is substituted once ormany times, whereby the substituents may be independent of one anotherand are selected from the group consisting of halogen and C₁-C₄-alkoxy;C₃-C₅-cycloalkyl or phenyl which is unsubstituted or is substituted onceor many times, whereby the substituents may be independent of oneanother and are selected from the group consisting of halogen,C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and halo-C₁-C₄-alkoxy; R₇signifies C₁-C₆-alkyl; either R₈ signifies C₁-C₄-alkylamino,di-C₁-C₄-alkylamino, C₃-C₆-cycloalkyl or C₃-C₆-cycloalkoxy; and R_(8′)signifies hydrogen; or R₈ and R_(8′), together signify unsubstituted orR₉-substituted C₃-C₄-alkylene, whereby one or two carbon atoms may bereplaced by O or N; R₉ signifies halogen, nitro, cyano, C₁-C₄-alkyl,halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₂-C₅-alkenyl,halo-C₂-C₅-alkenyl, C₂-C₅-alkinyl, C₃-C₅-cycloalkyl,C₃-C₅-cycloalkyloxy, C₃-C₅-cycloalkylamino, C₃-C5-cycloalkylthio,C₂-C₅-alkenyloxy, halo-C₂-C₅-alkenyloxy, C₁-C₄-alkylthio,halo-C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyloxy,halo-C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylsulfonyl,halo-C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino,C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkylaminocarbonyl or di-C₁-C₄-alkylaminocarbonyl; W is O or S; Xsignifies O or N(R₇); a signifies 1, 2 or 3; b signifies 0, 1 or 2; andc is
 0. 32. Compounds of formula I, respectively in free form or in saltform, according to claim 1, wherein A₁and A₂, independently of oneanother, signify aryl which is unsubstituted or is substituted once ormany times, whereby the substituents of A₁ and A₂, independently of oneanother, are selected from the group consisting of halogen, nitro,cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,C₃-C₅-cycloalkyl, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,unsubstituted phenyl or phenyl which is substituted once or many times;phenoxy which is unsubstituted or substituted once or many times; andpyridyloxy which is unsubstituted or substituted once or many times,whereby the substituents are each independent of one another and areselected from the group consisting of halogen, nitro, cyano,C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,C₃-C₅-cycloalkyl, C₃-C₅-cycloalkyloxy, C₃-C₅-cycloalkylamino,C₃-C₅-cycloalkylthio, C₁-C₄-alkylthio, halo-C₁-C₄-alkylthio,C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkylcarbonyl,halo-C₁-C₄-alkylcarbonyl and C₁-C₄-alkoxycarbonyl; or unsubstitutedhetaryl or hetaryl which is substituted once or many times and is boundby a ring carbon atom, whereby the substituents of A₁ and A₂ may beindependent of one another and are selected from the group consisting ofhalogen, nitro, cyano, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy,halo-C₁-C₄-alkoxy, C₃-C₅-cycloalkyl, C₃-C₅-cycloalkyloxy,C₃-C₅-cycloalkylamino, C₃-C₅-cycloalkylthio, C₁-C₄-alkylthio,halo-C₁-C₄-alkylthio, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino,C₁-C₄-alkylcarbonyl, halo-C₁-C₄-alkylcarbonyl and C₁-C₄-alkoxycarbonyl;R₁ signifies hydrogen, C₁-C₂-alkyl or halo-C₁-C₂-alkyl; R₂, R₃, R₄, R₅and R₆, independently of one another, signify hydrogen, unsubstitutedC₁-C₄-alkyl or C₁-C₄-alkyl which is substituted once or many times,whereby the substituents may be independent of one another and areselected from the group consisting of halogen and C₁-C₂-alkoxy; orC₃-C₅-cycloalkyl; R₇ signifies C₁-C₄-alkyl; either R₈ signifiesC₁-C₄-alkylamino, di-C₁-C₄-alkylamino; and R_(8′) signifies hydrogen, orR₈ and R_(8′) together signify unsubstituted or R₉-substitutedC₃-alkylene, whereby one or two carbon atoms may be replaced by O; R₉signifies halogen, cyano, C₁-C₃-alkyl, halo-C₁-C₃-alkyl, C₁-C₃-alkoxy,halo-C₁-C₃-alkoxy, C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyloxy,C₃-C₄-cycloalkylamino, C₁-C₃-alkylthio, halo-C₁-C₃-alkylthio,C₁-C₃-alkylsulfonyl, halo-C₁-C₃-alkylsulfonyl, C₁-C₃-alkylamino,di-C₁-C₃-alkylamino, C₁-C₃-alkylcarbonyl, halo-C₁-C₃-alkylcarbonyl orC₁-C₃-alkoxycarbonyl; W and X signify O; a signifies 1 or 2; b signifies0 or 1; and c is
 0. 33. Compounds of formula I, respectively in freeform or in salt form, according to claim 1, wherein A₁ and A₂,independently of one another, signify aryl which is unsubstituted or issubstituted once or many times, whereby the substituents of A₁ and A₂,independently of one another, are selected from the group consisting ofhalogen, nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy,halo-C₁-C₄-alkoxy, C₃-C₅-cycloalkyl, C₁-C₂-alkylthio,halo-C₁-C₂-alkylthio, C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl,C₁-C₂-alkoxycarbonyl, and unsubstituted phenyl or phenyl which issubstituted once or many times, whereby the substituents are eachindependent of one another and are selected from the group consisting ofhalogen, nitro, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy,halo-C₁-C₂-alkoxy, C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyloxy,C₃-C₄-cycloalkylamino, C₃-C₄-cycloalkylthio, C₁-C₂-alkylthio,halo-C₁-C₂-alkylthio, C₁-C₂-alkylamino, di-C₁-C₂-alkylamino,C₁-C₂-alkylcarbonyl, halo-C₁-C₂-alkylcarbonyl and C₁-C₂-alkoxycarbonyl;R₁ signifies hydrogen or C₁-C₂-alkyl; R₂, R₃, R₄, R₅ and R₆,independently of one another, signify hydrogen, C₁-C₂-alkyl orC₃-C₅-cycloalkyl; R₇ signifies C₁-C₂-alkyl; R₈ signifiesC₁-C₄-alkylamino, di-C₁-C₄-alkylamino; R_(8′) signifies hydrogen; R₉signifies halogen, cyano, C₁-C₂-alkyl, halo-C₁-C₂-alkyl, C₁-C₂-alkoxy,halo-C₁-C₂-alkoxy, C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyloxy,C₁-C₂-alkylthio or halo-C₁-C₂-alkylthio; W and X signify O; a signifies1; and b and c are
 0. 34. Compound of formula I, respectively in freeform or in salt form, according to claim 1, having the nameN-[2-cyano-1-(4,5-difluoro-4′-dimethylamino-2-biphenoxy)-2-propyl]-4-trifluoromethoxybenzamide.35. A method for the preparation of compounds of formula I, respectivelyin free form or in salt form, according to claim 1, whereby a compoundof formula II

which is known or may be produced analogously to corresponding knowncompounds, and wherein R₁, R₂, R₃, R₄, R₅, R₆, R₈, R_(8′), R₉, W, X, A₂,a, b and c are defined as given for formula I, is reacted with acompound of formula III

which is known or may be produced analogously to corresponding knowncompounds, and wherein Ar₁ is defined as given for formula I, and Q is aleaving group, optionally in the presence of a basic catalyst, and ifdesired, a compound of formula I obtainable according to the method orin another way, respectively in free form or in salt form, is convertedinto another compound of formula I, a mixture of isomers obtainableaccording to the method is separated and the desired isomer isolatedand/or a free compound of formula I obtainable according to the methodis converted into a salt or a salt of an compound of formula Iobtainable according to the method is converted into the free compoundof formula I or into another salt.
 36. A method for the preparation ofcompounds of formula II, respectively in free form or in salt form, e.g.characterised in that a compound of formula IV

which is known or may be produced analogously to corresponding knowncompounds, in which R₂, R₃, R₄, R₅, R₆, R₈, R_(8′), R₉, W, X, A₂, a, band c are defined as for formula I, a an inorganic or organic cyanideand a with compound of formula R₁—NH₂, which is known or may be producedanalogously to corresponding known compounds and wherein R₁ is definedas for formula I, and if desired, a compound of formula II obtainableaccording to the method or in another way, respectively in free form orin salt form, is converted into another compound of formula II, amixture of isomers obtainable according to the method is separated andthe desired isomer isolated and/or a free compound of formula IIobtainable according to the method is converted into a salt or a salt ofan compound of formula II obtainable according to the method isconverted into the free compound of formula II or into another salt. 37.Composition for the control of parasites, which contains as activeingredient at least one compound of formula I according to claim 1, inaddition to carriers and/or dispersants.
 38. (canceled)
 39. Method ofcontrolling parasites, whereby an effective amount of at least onecompound of formula I according to claim 1 is used on the parasites.40-41. (canceled)
 42. A method for controlling parasites comprisingapplying to said parasites or its habitat a parasiticidal effectiveamount of at least one compound of formula I of claim
 1. 43. The methodof claim 42 wherein said parasiticidal effective amount of said at leastone compound of formula I of claim 1 is administered to an animal hostof said parasite.
 44. The method of claim 43 whereby said at least onecompound of formula I of claim 1 is administered to said animal hosttopically, perorally, parenterally, or subcutaneously.
 45. The method ofclaim 42 whereby said compound is in a formulation consisting of thegroup of pour-on, spot-on, tablet, chewie, powder, boli, capsules,suspension, emulsion, solution, injectable, water-additive, andfood-additive.
 46. The method of claim 42 wherein said parasites areendo-parasites.
 47. The method of claim 46 wherein said endo-parasitesare helminthes.
 48. A method of treating an animal for parasitescomprising administering to said animal in need of treatment thereof aparasiticidal effective amount of the composition of claim
 37. 49. Themethod of claim 48 wherein said administration to said animal istopically, perorally, parenterally, or subcutaneously.
 50. The method ofclaim 48 wherein said composition of claim 37 is in a formulationconsisting of the group of pour-on, spot-on, tablet, chewie, powder,boli, capsules, suspension, emulsion, solution, injectable,water-additive, and food-additive.
 51. The method of claim 48 whereinsaid parasites are endo-parasites.
 52. The method of claim 51 whereinsaid endo-parasites are helminthes.